#1041: “How do I get my much older work ‘friend’ to stop messaging me late at night to talk about his relationship problems?”

Dear Captain,

I have a colleague, “Peter”, who I’ve known for several years. We first worked together at a festival, and added each other on facebook/phone for organisational reasons, as he was the crew leader. Over time we have become friends, although I do see him as more of a colleague as he is 20 years older than me with a kid, and I’m a student. I worked with Peter again this year, and during the festival he split with his girlfriend. Naturally he was upset, and I was sympathetic – at first.

Recently, he has been pestering me on social media, and on the phone when I ignore his messages. I shouldn’t ignore him, but he frequently sends me random unsolicited updates on his life/ weirdly personal accounts of his break up, often at 2am, and I don’t know how to respond. Sometimes I will commiserate, but then he will turn on me and ask these loaded passive aggressive questions like “you really ok with this?” or “am I being obtuse”, so I have stopped responding as I don’t have the time or emotional energy to deal with him right now.

I think he is just looking for a friendly ear, but I’m struggling to deal with someone who is so emotionally vulnerable and so different from me. When I do respond, we get our wires crossed, so I try and keep my replies neutral. For example, he had been trying to recruit my young best friend to his crew, and even after I said she wasn’t interested multiple times, he added her and starting talking to her on social media. I got annoyed at him over boundaries and he got in this huge strop about how he could do what he liked. Then he eventually apologised, but the rift keeps widening.

Peter constantly questions how deep our friendship really is, and to clarify, I have always seen him as a friendly work colleague. From my point of view, him pouring out all these emotions on to me seems very strange, as surely he must have closer confidantes his own age? I probably sound quite cold, but I don’t think he should be discussing the legal issues and horrible drama of his break up with me.

I want to maintain our good working relationship, but don’t know how I can enforce boundaries, particularly on social media. Help!

She/her pronouns please. 

Hi there:

You are not selfish if you don’t want to have these conversations anymore. Let’s ask some questions of the situation:

  1. Would Peter send male colleagues -his boss, say, or male colleagues who are his same age & peer status – messages like this? (To be clear, if he does, that doesn’t make it okay, but when gender/power shit gets weird at work it’s good to use this as a reality check.) If he did overshare with these guys, would they be like “right on Peter, that’s a totally normal thing to do, pip pip cheerio!” No, they would find it weird and they would either avoid the messages (and him) or tell him to knock it off.
  2. Is Peter doing even a tenth of the emotional labor around this situation you are? By which I mean, you are worried that if you say no you’ll lose your friendship and affect your professional life. Why isn’t he worrying that dumping his relationship problems on a college student will affect his friendships and professional life?
  3. Are you happy and comfortable with the situation and do you want it to continue?

#3 is the one that counts.

Peter is 20 years older than you and you’re a student (seasonal/festival?) worker where he works. He 100% fucking knows that it is inappropriate to message junior female colleagues at 2 am to tell them about his relationship troubles and to constantly put you in a situation of having to reassure him that it’s all okay when it isn’t. I also think it’s likely that Peter seeks out “working”/social media friends relationships with very young women (like you, and your best friend) because he likes the weird power-imbalances and ambiguous situations. There’s an element of grooming behavior going on here that I do not like. Over the last year I’ve read a ton of stories about sexual harassment at work (especially in universities) and “It started with him confiding in me about his romantic life and contacting me a lot outside work hours wanting emotional support” is a common thread in a lot of the stories. A lot. It’s the old “my wife doesn’t understand me, not like you” trick dressed up for a new generation. I need all young people everywhere to recognize this shit for what it is and to learn the response “Huh, that’s sad, but let’s stick to work topics!” when someone tries that with them. #LysistrataTime

When Peter asks stuff like “are you really ok with it?” it’s a rhetorical question. When he calls himself obtuse, it’s so that you’ll jump in to say he isn’t. He’s trying to reassure himself that what he’s doing is ok when he knows that it’s probably not. But he *is* asking you, so, you do have an opening to take him at his word and not at the intention you’ve (correctly) picked up on: “Hey, since you ask, I’m not really comfortable hearing about this kind of personal stuff. Let’s stick to lighter stuff, or better yet, work!

You did the right thing by not responding to messages when you didn’t want to engage. If you’re not ready to block or unfriend Peter entirely yet online, use filters and massively limit his ability to monitor your feed. You can also check a setting on Facebook Messenger that lets you ignore messages from a given person. I recommend deploying it immediately. To him it will look like you are rarely or never around.

And the next time he “pesters” you about his relationship troubles, tell him the truth:

Peter, I know you’re hurting, but I’m not comfortable being your sounding board about this anymore. I’m sorry I didn’t tell you so sooner. I’ll see you at work.

See also:

  • “I hope things get better, but I don’t want to hear about [girlfriend/breakup] anymore.”
  • “I did ignore your messages about [problem] because I have no idea what to say and I wasn’t comfortable with the personal direction of the conversation.”
  • “I see you as a friendly person to work with, and our working relationship is really important to me.”
  • “I see you as a friendly work colleague.”
  • “You’re my work friend. I really like working with you, but this is too much.” 
  • “I like working with you but this conversation is too personal for me.” 
  • I like working with you but I don’t think it’s working for me to mix social media and professional stuff.” + (The block button)

A friend would say “I understand and I’m so sorry I made you uncomfortable” and end the conversation, because a friend understands that you are not a 24 hour emotional labor vending machine and that you get to say no to things.  At minimum, a Grownass Professional Man Who Is Not A Creep would say “I understand and I’m sorry I made you uncomfortable” and then he would end the conversation because he understands that you are not a 24 hour emotional labor vending machine and that you get to say no to things.

When creeps and bullies are told to stop doing something, they use “negs” or “typecasting” as manipulation tools. They say stuff like “Whoa, I didn’t realize you were so uptight,” “I thought you were mature and you could handle it” or “I thought age doesn’t matter in friendship like ours” or “You’re right, I’m so pathetic, how can you even stand me?” (stealth version, trying for pity) or “But I asked if it was okay and you didn’t say anything, so it’s not fair that you would ask me to stop now” to try to get you to defend yourself or comfort them by doing what they want you to do/what you don’t want to do. The fact that you don’t like this and don’t want it to continue cancels out any argument he might make.

One way to defuse typecasting tactics like this is to agree with the neg instead of arguing with it, for instance:

  • “Yep, I’m pretty uptight, and also, I’m not okay with this anymore.” 
  • “You’re right – I’m a college student, and this is too mature/too much for me to handle, so, let’s stop talking about relationship stuff.” 
  • “Yep, you did ask if it was okay, and I’m so sorry, I should have said something sooner. But I’m saying something now, so, are we cool?” 
  • “Yep, it’s probably unfair, but it’s what I want to happen now. Good talk, everyone!” 

If Peter feels sad or embarrassed about how he’s behaved, well okay, I would feel embarrassed to know I was weirding out a friend or colleague the way he is doing. Let’s get even more specific: I’m in my 40s and I work with college students who are 20-25 years younger than me all day long. They are hilarious and talented and great, and some of them do become friends on social media after the class is over. I promise you, I PROMISE YOU, I would be completely fucking mortified if I started using one of them as a witching hour sounding board about my romantic ups and downs and asking them to constantly reaffirm the closeness of our friendship. Like, I cannot imagine circumstances under which this would be at all normal or ok or even possible. Peter’s embarrassment or hurt feelings at doing an embarrassing thing are not your responsibility to fix. If this all goes south, it’s not because you’ve been unprofessional or mean. “I like working with you, but I’m not enjoying these 2AM feelingsdumps about your smoking ruin of a love life” is not what he wants to hear, but it’s also not a mortal insult. A sincere “Hey man, I hope things get better, but I am not the right sounding board for this” + “Sooo, what kind of weather are the sports teams are having this week?” is a reasonable, normal and and friendly boundary to set.

Your friendly working relationship might deteriorate further if you speak up, not because you did anything wrong, but because I don’t have high hopes for Peter’s emotional maturity or professionalism. He’s shown you that he has pretty poor boundaries and has a hard time taking no for an answer (that whole thing with recruiting your friend!) and I predict that when you tell him to back off he will dump a big old sulk on you. Not only did his girlfriend leave him, but also his cute nice source of endless emotional labor is also bailing and his self-image as a person who is good with The Youth took a hit. Let him sulk. Give it time. He’ll either decide to be cool or he’ll make it undeniable that you can’t be friends.

If Peter threatens your job or retaliates professionally in any way when you withdraw from personal conversations with him, launch his ass directly into the center of the sun report him to Human Resources. Screencap everything he’s sent you as backup, and document that you asked him to stop and how he responded. Telling HR “We were friends but then he started expecting me to comfort him about his love life at all hours. I did my best to listen for a while because I thought of him as a friend as well as a coworker, but when I asked him to stop he made it super-weird and threatened to make sure I never got hired for another festival” is not gonna make him look good. To be clear, I wouldn’t necessarily start with HR – try telling him directly first, even if it just ends up being good boundaries and assertiveness practice for you. Please know, also, 100% this guy does not have the power to make or break your career. If he implies anything of the sort he’s an even bigger douche than I already think he is.

I’m sorry you’re having to deal with this but I want you so much for you to know and understand: To me, Peter’s behavior is part of a recognizable and predictable pattern of older men demanding emotional labor and crossing boundaries with young employees, especially young women. He hasn’t tried to have sex with you or date you…yet…and he may never actually do that, but I feel like it’s brewing in his mind to think of you That Way. In your shoes, I would not be alone with him, I would not drink around him, I would not hang out with him late at night, I would not let him be my ride to and from anything, I would lock down my social media feeds (especially anything with photos of you) & I would tell my friends about this weird older guy at work who tried way too hard to make a friendship happen. Paranoid? Maybe. Just remember how we fight negs: “Yep, I’m a little paranoid, but also, I don’t want to suddenly feel that guy’s hand on my knee, and he’s already shown me that he’s not really good with boundaries.” We don’t have to have a jury trial for you to decide not to hang out with someone or to exercise caution when you do.

I also want you to know that you didn’t cause any of this by being friendly to him. Peter has a lot of choices about how he behaves. I hope he’ll do the right thing  – “Whoa, sorry I made you uncomfortable, of course I’ll take it elsewhere” –  and then continue to be a good colleague. If he doesn’t, none of it is your fault. A friendship where you can’t state a boundary without retaliation or “ruining the friendship” was never a friendship.










253 thoughts on “#1041: “How do I get my much older work ‘friend’ to stop messaging me late at night to talk about his relationship problems?”

    1. Seriously, anyone who says stuff like “it’s a free country, I can do what I want” when someone tries to enforce reasonable human boundaries is an asshole.

      1. “It’s a free country, I can do what I want” is kindergarten BS. It’s what you say when you’re a little kid and want to eat candy for breakfast and not take naps. Any grown adult who uses this argument needs a time-out.

        1. TBH I’m an adult who has said this, literally because I wanted to eat candy/cupcakes/ice cream for breakfast. So this guy really doesn’t have a good argument.

          1. An adult CAN eat candy/cupcakes/ice cream for breakfast, because they already know how it will affect them, and they’re probably not hurting anyone but themselves. And if they do wind up hurting others by becoming sugar-monsters, and others point it out, adults (and by that, I mean actual mature people) will take responsibility for it, and change their behavior.

            A child doesn’t know better and usually becomes a royal pain for everyone in the vicinity, if they eat all that sugar for breakfast and completely lose control.

            That is the difference.

      2. This is the sort of person who thinks that being told to not use racist/misogynist/homophobic rants is “censorship”.

      3. To paraphrase someone else (I forget who): If the best argument you’ve got is that what you’re doing isn’t technically illegal, then you’re an asshole.

      4. Ahaha I had a guy pull that with me on the street, once. He stopped to chat with me and I went along with it because I actually like living in a world where I can have random chats with strangers, and then I said “welp, better get these groceries home” and he said “I will walk you home” — no, literally, did not even ask, just said he would. So I said “no, thank you” on grounds that it is polite to pretend the other person was polite even if they were 100% not, and the polite thing for him to have done would have been to ask, dammit, and he goes and pulls out “It’s a free country, I’m allowed to be on the street, you can’t stop me.”

        Well, jeez, I had to let that one sit for a couple of seconds. Finally I conceded that, indeed, if he really wanted to, he could force his company on me, all the way home. Did he really want to do that?

        He thought about it for a moment and decided that he would not, and I confess that I have always looked back on this episode with the gleeful satisfaction of a rationalist who has actually succeeded in arguing somebody out of being a total jerk, because that never happens. (He gets no credit for his change of heart. I am taking all the glory to my brilliant persuasion skills, dammit.)

        1. That is excellent! I feel like I don’t hear enough stories of people showing creepazoids just how creepy they are. Well done.

        2. It may have been less about rationality, more about standing up to him and refusing to pretend that what he’s proposing is okay. Which is just as good!

    2. Right on the nose. That was also quite the flag for me because of a specific dude I used to be internet friends with.

      One day, I asked that ex-friend of mine (who suspiciously fits the profile described here – almost 20 years older than me, expected buckets of emotional labour around the clock, and constantly questioned our friendship) to stop calling me “hun”, “cutie” or “sweetie” because the romantic connotations made me incredibly uncomfortable. Also because I hate that sort of cloying, infantilizing names (I’m short and I look young and I’m sick of not being taken seriously).

      He threw a tantrum, called me ridiculous, and blocked me. Then, when he contacted me again, he accused me of hurting his feelings and of manipulating him as part of some power trip. What I remember most is when he said, very matter-of-factly, “I’ll call you whatever I want”, like this was utterly non-negotiable, like I had no say whatsoever in the matter. It was scary and infuriating in equal measures.

      I eventually found out he actually did have feelings for me and that he had been hoping to visit my city soon…and sleep at my place. When I told him I wasn’t interested, he said I was being unfair and discriminating against him because he has a kid and is almost twice my age. Yeah.

      We’re no longer friends, and this is how I learned that this kind of behavior is one of the early warning signs of Rampant Entitlement Syndrome.

      1. “he said I was being unfair and discriminating against him because he has a kid and is almost twice my age.”

        I’ve heard that one too many times. Friendships and romance are not subject to anti-discrimination laws. If you don’t click, you don’t click. I got fed up of pointing out there are plenty of other people in the world happy to date people with children and people older than themselves and the not-so-humble dating petitioner should seek those people out instead of making me out to be an intolerant person for not ‘giving them a chance.’ No chemistry = no chance!

        1. Yeah, exactly! It’s not like I was madly attracted to him and was holding myself back with the “twice my age and has a kid” stuff. I wasn’t into him, partly because he seemed at a very different life stage than me, and partly because, well, I wasn’t attracted to him as a person.

          Fuck the idea that middle-aged men (I’m sure this applies to everyone, but I’ve mostly seen men do this) are entitled to date women half their age and that said women are intolerant for refusing. There’s just so much problematic and sexist behaviors baked in that mindset that it would take hours to unpack.

      2. “I’ll call you whatever I want”

        Gosh, I can’t imagine why you didn’t snap him up. He seems like a real catch.

        “When I told him I wasn’t interested, he said I was being unfair and discriminating against him because he has a kid and is almost twice my age.”

        Bet you a tapas dinner this dude would blithely discriminate against women his own age, and certainly wouldn’t ever consider women older than him. But sure, cool, bro, call the EEOC. See how far that gets ya.

        It’s almost as if we are things these guys are entitled to and not human beings. I can’t imagine why they have a hard time dating.

        1. (Omg it’s Sheelzebub /swoon)

          You guessed it – actually a lot of the emotional labor I used to engage in with this dude was to try to convince him that he wasn’t condemned to die alone and unloved just because he made it to 40 as a single dad. I even showed him stats indicating that in his state, the majority of single people his age were also parents. Which, yknow, probably means many women around his age wouldn’t mind dating a man with a kid.

          Obvs that didn’t help because as you astutely guessed, he was looking to date a younger woman. The issue was that he felt having a child was a turn-off for younger ladies. When I suggested that maybe, then, he should consider dating women closer to his own age, because they’d be more likely to be chill with his life situation, he interpreted it as me saying he had to lower his standards. I was aghast.

          Yeah, it really deserves to be said and repeated – fuck the idea that middle-aged men are entitled to date women half their age. I deeply resent the notion that the value of a woman goes down as her age goes up. I

          1. And fuck the double-standard idea that women have to lower our standards and date him. Seriously:if dating someone this guy’s age is lowering one’s standards, he’s being really unreasonable in expecting women to do that for him.

            Further cynical thought: he was probably looking for someone who was willing to be a stepmother to his child, but wasn’t willing to be a stepfather to that woman’s children.

      3. Ugh, this reminds me of my former boundary-crossing (older, male) colleague. One day he walked into my office and said, “What’s up, girlie?” to which I immediately responded, “Please don’t call me that; I prefer to be called by my name.” He immediately went into why I was wrong, so I turned back to my desk, got back to work, and refused to respond. He spent most of the rest of the day throwing a tantrum about it, returning to my office repeatedly to “see if [I] was over it” and make snide remarks to my office mate. I refused to engage at all, which apparently drove him nuts, but I had already said what I had to say and didn’t think I should have to explain to him why he shouldn’t call people names they don’t like to be called.

        He did eventually apologize and agree that calling your co-workers “girlie” in the office is perhaps not appropriate, although he clearly thought I was ridiculous and over-sensitive.

        I won’t get into the time he showed up at my apartment on a Sunday and drunk…

      4. “I’ll call you whatever I want”

        Then he surely won’t mind if I call him Creepy McFuckOff. Since, ya know, it’s a free country.

      5. I have seen so many men Lose Their Shit over being asked not to use pet names. It is bizarre to me how some of them are SO ATTACHED to the idea that if we just say “please call me by my name and not ‘hon'” we’re suddenly “crazy psycho bitches.”

        1. Well, see, then they might have to remember our names, which might lead to the horrifying conclusion that women are individuals with identities that extend beyond “look pretty and do whatever a man happens to want at that moment”.
          A recent live episode of the podcast My Brother, My Brother and Me had a woman say that whenever a guy calls her by a ridiculous pet name at work, she responds by calling him “champ”, “slugger”, “tiger”, etc. This woman is officially my hero.

        2. I know I’m generalizing and it certainly doesn’t juuust apply to dudes, but I’m aware that many men just aren’t used to having their behavior questioned at all. And I do think that the sexism in our society makes it easier for men to arrive to adulthood with that trait.

          Like…if I compare my male friends to my female friends, I can’t help but notice that the women seem to spend a lot more time wondering if they’ve said something wrong, if they’re annoying, if they’re problematic, if they should change their look/the way they speak/their attitude/their mindset/their entire personality. My guy friends on average appear less eager to reconsider everything about their life everytime someone reacts negatively to them. Good for them – I can only wish I had that sort of confidence – but I do think that it can create shitty behavior if not coupled with a good measure of self-awareness.

          I think the pet name thing is part of that. Some men are so used to being “allowed” to just do or say whatever they want, without consequences (social or otherwise), that the instant someone points out they did something wrong, they fly off the handle. Likely because they’re not used to feeling self-doubt, or aren’t familiar with the kind of guilt that comes from having behaved like an ass without realizing it. So their reaction is to blame the person they disrespected, because if they can convince everyone (and themselves) that the person was just oversensitive and psycho, then, it means they don’t have to examine the guilt and self-doubt. Which in turn means they don’t have to change their behavior. Which is nice! No effort has to be expanded. Statu quo maintained.

          A lot of hurtful defensive behavior, I think, comes from this particular type of emotional laziness – the unwillingness to doubt oneself because it’s uncomfortable and can lead to the effort of changing.

        1. My guess is that they’re sexist as heck, and thus believe that after 30, women are not longer Pretty Young Things and thus are worthless. Either that or women their own age aren’t willing to put up with their bullshit…

          1. Many of them are aware that women their own age are more likely to be wise to their manipulative and creepy behavior so they filter for that by going after much younger women. One of the many reasons I’m glad the internet exists and we can educate and warn each other about the red flags.

          1. EXACTLY! Sorry, but as an Old, ain’t no way I’m putting up with a whiny, entitled jerkwad who thinks he can patronize women of any age and get away with it. Hard pass.

      6. “What I remember most is when he said, very matter-of-factly, “I’ll call you whatever I want”, like this was utterly non-negotiable, like I had no say whatsoever in the matter. It was scary and infuriating in equal measures.”

        “I’m so glad we’ve agreed upon this system. I’m going to call you a ‘former friend.’ Dick!”

    3. Right? What kind of guy who is “aware of boundaries” and not a creep, hops up and down, shouting, “I can do what I want to and you’re mean for saying no!” When people respond to a simple “No, stop that.” with a temper tantrum, they are not a person with good intentions.

  1. I just wanted to offer you some validation around this, OP:

    ” I shouldn’t ignore him, but he frequently sends me random unsolicited updates on his life/ weirdly personal accounts of his break up, often at 2am, and I don’t know how to respond.”

    This is precisely when you SHOULD ignore him and have every right to. He is acting far outside professional bounds and even personal friendship bounds: most people understand that you don’t text anybody but your very closest friends and family at 2am, about anything, ever. This person is acting inappropriately and you don’t need to feel any obligation to respond at all. I know we are programmed to be nice to people, especially when they are sharing something painful, but he is not being nice to you, so you don’t need to be nice back.

    1. Yes to all this. And as an Old, I want to emphasize that it is pretty unusual for someone approaching 40 (doing a rough calculation from the LW’s statements) to text friends and acquaintances as a matter of course at 2am. This guy’s same-age peers probably have steady 9 to 5/6/7 jobs, with increasing responsibilities therein. They probably have children who have to get up early for soccer practice. (Nothing wrong with them if they don’t have these things, of course.) They’ve probably learned how to self-soothe, or at least how to sit with uncomfortable feelings like loneliness and anxiety. At the very least, they’ve learned that using friends as emotional dumping grounds is a fast way to lose them.

      So this guy’s same-age peers are not going to be receptive to his texts. They wouldn’t have the time or energy for them, and they wouldn’t have the empathy for them either, because they’d figure he’s demanding emotional work from them that he should have figured out how to do for himself a long time ago.

      So what does a guy like creepster do? He hunts around for someone whom he believes is less likely to perceive how much he’s demanding, and/or less likely to cut him off. Ding ding ding — young person he works with, who is socialized (as many people raised as girls are) to be “nice” and to put their own needs aside so as not to hurt other people’s feelings.

      1. Another Old here – I’m in my early 40’s and I actually have the same age difference with some of my friends as LW has with this Peter dude – and I entirely agree with this. If I’m going to send someone a non-emergency update in the wee hours of the morning, I will use email, Facebook, or some other method that isn’t likely to wake them. Even my friends who are night-owls and are probably awake anyway.

        (I do receive and respond to 2am texts, but I have the aforementioned younger friends/classmates as well as friends who work in the restaurant and entertainment industries and sometimes respond to texts from me when they get home from work. They all know I’m ok with it.)

        1. Also an Old, and one with young-ish (early to mid-20s) boarders. We’re friendly as well as landlady/tenants, and I have made it unspeakably clear to them that if they are ever out having a good time and get just a LITTLE too drunk, or they lose their wallet/are robbed, or they walked/biked and some time between departure and planned return the weather turned crap and it’s not safe for them to be on the road in bucketing rain or lightning, that they can call me and I will come get them at any time of the night, no questions asked.

          Otherwise, unless something is on fire, someone is in the hospital, or it’s an expected call from work when I have on-call rotation, do NOT call me after 8:30pm or before 7am.

          I have friends and work colleagues who live outside my time zone, some of whom are not even located in the same hemisphere as I am, and even they know the time differences and when I’m going to be awake.

          This dude knows what he is doing. And he knows that what he is doing is not OK.

          1. And you bring up another excellent issue:

            In this age of global instant communication, if you absolutely need a sounding board at 2 in the morning, get online and find a friend in another hemisphere, who is wide awake at that time.

            Australia’s good.

      2. I’m an Old too. At that hour of the night you hear from people because someone’s died or in hospital. Seriously! I have one person I might talk to on FB Messenger at that hour – an ex who is a fellow insomniac – but neither of us assumes the other will answer, and we certainly don’t escalate to phone calls. It’s usually just an amusing message that will be seen at some later hour.

        Even current sexual partners can’t assume conversation after hours, and I don’t assume I could contact them.

        He is taking liberties, big time.

        (Pro tip: telling him that 2AM messages are only okay in a dire emergency doesn’t work. He will simply start claiming he is have a dire emergency every time he wants to talk to you).

        And like many other commenters here, I also wish I could redo my 20’s.

        1. That’s when you start answering every after-hours call with “Who died?!” If nobody died, you hang up.

          You know, I miss the old phones you could really slam down. Hanging up with extreme prejudice worked so much better when you weren’t worrying about breaking the touch-screen.

      3. Yes, I am also heading for Old. The last time I got in touch with anyone at work at 3 AM, it was an email to say “I am having a medical emergency; would someone please go at 8 to take care of Essential Thing Which Must Happen At 8 AM?” The only person I text at 2 AM is my sister, who lives in a 7-hour-ahead time zone. This guy is a creep, this is not normal, and you do NOT have to put up with it.

      4. As a fellow Old, I cannot co-sign this enough.

        And if I do have late night text discussions with friends, they are NOT whining at my junior colleagues about my personal life. Ever.

        Dear LW, please screencap everything this obnoxious manbaby sends you.

      5. Another Old signing off on this–dude is creepy and you should totally ignore his 2am texts.

        Relatedly: I have an app on my phone for personalized text notifications. This also allows me to know immediately whether I need to pay attention to a text or not, because I know who it’s from. Texts that are not from people on the list of people with personalized notifications…are silent. Additionally the app includes quiet time settings, so I can set both quiet hours and who gets silenced during these quiet hours. This app is why the friend who doesn’t sleep and texts me at 3am with random thoughts is still alive, and entirely worth the $2.99 I paid for the deluxe version.

      6. I think I’m technically between a Young and an Old.

        I have two male friends (from work) who are an Old. Their texts or messages can best be described as “infrequent,” “midday,” “100% relevant to shared interests,” and “not requiring a response every single time.” Because I’m pretty sure they think I’m a person.

    2. In my opinion it is very similar to drunk dialing except utterly inexcusable because he is not drunk. Drunk is a very poor excuse for trampling the boundaries of acceptable human interaction, but it is an excuse. This behavior is inexcusable.
      People who refuse to take no for an answer are not safe to be around.

    3. I mean, I don’t mind if people want to hang out and talk at 2 AM personally, but that’s because I’m usually awake at that time anyway. Peter texting at 2 AM offers the gold-plated, diamond-studded excuse of I Was Asleep. (Opportunity to reinforce boundaries: “I’m not sure you realized – I know how time can get away – but sometimes you text me very late. I’m really not going to be on Messenger past midnight, or answering my phone.”)

    4. Yes!!!! The 2am stood out, as did the side project of recruiting your young friend, and to snark at you. He showed you who he is: believe him! He is a man who believes he can be offensive and inappropriate whenever he likes. Maybe a bkgd check for prior restraining orders or deviant behavior might be in order. I’m in my 40s also and I do NOT view the kids in their 20s at work as confidants they are kids! To me anyway. They’re smart and fab and age appropriate but not equals. And I can’t even imagine creeping on a friend of theirs! Grooming is right the Captain is once again spot on. Please stay away from this guy and be prepared for a big can of crazy when you try to set boundaries. I’d run this by HR. Hopefully there will be a lovely older woman there who will be appropriately horrified on your behalf. And once this guy realizes you’re not in for the grooming he’ll turn on you but he may also (esp if he’s got a history of this, which I suspect) dial it back and go away. Bc you may not realize how bad this is but be assured he does!!!!

      1. Endorsement by another Very Near Old. And even as a Young, I did not send text messages at 2 am for work purposes. I was either asleep or Up To No Good.

  2. “I shouldn’t ignore him”

    Yes you absolutely positively should.

    Let me give you what I think is the most generous possible read here, based on my personal behavior between teen and early twenties when I finally got treatment for my depression: it was not uncommon for me to latch onto someone who’d been generous in their time and support. Being depressed and unable to handle my bad feelings, they’d be a dumping ground for my need to vent. They were probably one of the few places I had to seek support because I’d alienated most other people with my barrage of negative BS which I never did anything to actually FIX. Maybe I’d develop romantic interest in them and, in my depression, they’d start to seem like some kind of Solution for my issues.

    I didn’t mean any ill by it. I had problems, which really was, for me, just one problem: a need to treat my depression. I’d like to think that, appropriate intimacy level issues aside, I was as well-mannered and not-creepy about it as you can be. Which isn’t very. But ya know, so what? It wasn’t on these people to be my savior. It wouldn’t have been on a particularly _close_ friend to be my savior either. I was asking too much of these people and even if they’d given everything I was asking of them and more it still wouldn’t have fixed my problem.

    The most generous possible read is that Peter is in the space I was in and might find his way to get his act together and be a better and happier person. Maybe that’s depression like it was for me. Maybe he needs counseling to deal with his relationship issues. Whatever he needs – and it’s not for sure he’s not actually just a jerk trying to groom you for sexytimes – you can’t provide it. So cut him loose with a clear conscience: you don’t owe him what he’s asking of you and, in the most innocent possible interpretation of his behavior, the sooner he comes to realize this is a counterproductive way for him to try to fix his life the sooner he can get some help/make some changes that will actually work.

    1. I knew someone once who was well described by both Tepid Tea and Don Whiteside’s comments above. And, LW, fwiw, even this guy in the very throes of fitting those descriptions once said, “At least I don’t call at 2am! You’d tell me to get lost and never speak to me again and I’d deserve it!”

  3. Mostly I agree with the captain. Start with these scripts. If possible, get them in writing with time-stamps; email is great because it’s easy to file, search, and retrieve, but texts or other messages are better than nothing. You want hard evidence that you told him you weren’t comfortable and told him to stop. Hopefully he’ll listen!

    If that doesn’t work, though (and it might not–Peter has shown a tendency for ignoring clearly set boundaries before), I don’t think you should wait and see if he tries to retaliate. If he’s consistently refusing to acknowledge your boundaries even after you’ve set them clearly, that’s plenty to start pulling in extra support. Do you have HR? A sympathetic manager? A mentor (either a formal one or an informal ‘person who has been around a long time and gives me advice’ one), especially a woman who is familiar with the dynamics of being young and female in your workplace? Pick whichever is both available and the most likely to be helpful to you, based on what you know of your workplace.

    Tell them, “Lately Peter has been sending me a lot of really personal messages at all hours. I’ve told him I want to keep our relationship limited to professional circumstances and asked him to stop, but he’s ignoring me and continuing. It makes me really uncomfortable, and at this point it’s bordering on harassment. What’s the right path for handling this here?” If they try to tell you it’s not that bad and you should just tolerate it (they shouldn’t, but this happens sometimes), don’t accept that. “It might not sound like that big of a deal on the surface, but it’s getting really invasive. I’m disturbed by how he’s ignoring my requests for him to stop, and I’m worried he might escalate.”

    At the very least, if he does try to retaliate or otherwise escalate, you have both written records that this is an ongoing problem and people who you’ve discussed the problem with. Those are both really useful if you need to prove this problem exists at some point. Hopefully it never escalates to that point, but I’d rather be safe than sorry, especially with a guy who’s shown serious tendencies towards ignoring young women’s boundaries before.

    1. OP, if you’re going to take this route – and I don’t think it’s a bad idea – you should also mention what happened with your friend. That strongly suggests this isn’t just a case of Peter misreading the nature of his relationship with you, or just looking for sympathy: he has serious, systemic boundary issues that affect how he does his job, and those should be addressed before they affect anyone else.

    2. Seconding the “get it in writing”. If he’s cool, it doesn’t hurt and if he’s a asshole, it’s good insurance.

    3. Another point to bring up is to explicitly say, “I’m worried that this might impact my work here–that if I brush him off and he decides to punish me for it, he can make it uncomfortable here, or he’ll gripe about me and ruin my reputation here. How can I avoid that?” Drag everything out into the open–all the worries and risks. Don’t assume people will read between the lines, etc. Be direct and thorough.

      I’m an older person at my job, and I’m a manager with a good reputation with my people. If ANYone in my company, not even in my department, came to me for help, they would get calm, confident, proactive advice; someone who would accompany them to HR; someone who would speak for them to their own manager.

      So when you’re looking for someone to advise you, look around–all the way around.

  4. I wish I had heard all this 15 years ago. It would have saved me a lot of discomfort, uncertainty, and disappointment.

    It’s so depressing how common this is.

    Bring on Themyscira. Can’t wait to learn how to javelin.

    1. Uuuugh the “Peters” of the world.

      I’ve had an almost miraculously creeper-free life, but about ten years ago? This. One. Guy. The oversharing about his failing relationship. The cutesy uninvited boundary-pushing. I’ve cut off all contact but he’s still a community leader in my Hobby Thing, so I can’t act as though he doesn’t exist. LW, I wish I had this advice then. It would have saved me a lot of time and heartache caring about what this guy thought of me.

      I’d be headed to the gymnastics-equestrian-archery range, myself.

  5. Everything the Captain has said here is dead on. I have had, let’s say, “several” instances of older men using the breakdown or breakup of a romantic relationship as a means to upgrade me from fellow-tabletop-roleplayer or friendly acquaintance or what-have-you to Vaguely Girlfriend Shaped Object. I even once had an older dudely “buddy” use my attempt to get advice about my horrible then-boyfriend as a launch to “okay let me touch your butt now that you are sad.”

    It’s depressingly common for older dudes to do this to folks who are younger and of marginalized gender. They especially love to do this to femme-identifying or -appearing individuals. Such gross men like to make it about “maturity” while not even remotely seeing the hypocrisy. “Sure dude, I’m not mature for my age. Cool. So go find somebody your own age to bounce this off of.”

    Depending on what you ultimately want here, LW, it’s a difficult to win situation. I’m in my early 30s now, but faced a lot of this sort of thing in my mid-teens to early 20s. There has been one situation out of probably 6-8 that managed to go back to the sort of friendship we had before. And that was because we didn’t talk for 3 years and during that time he got therapy and started dating in his own age range.

    I really want to make sure you know that zero percent of this is your fault. It’s not you “making it weird” by not wanting to be the free counselor of a much older guy. You’re not “being mean” by wanting to keep your coworker as “just” a work friend. If this ends up requiring you to block him on everything, you’re not “overreacting.” None of this says anything about your maturity or compassion or friendship skills. If anything, the fact that your alarm bells are ringing and that you didn’t shout at this dude when he *went over your head to solicit your best friend when you told him not to* says that you have a compassionate, good head on your shoulders.

    As I’m sure you’re about to see from other posts, this experience is everywhere and this behavior is insidious. I’m sorry this is happening and that your colleague is acting like this.

    1. Agree with all the good Captain said but also had to +1 this:

      “zero percent of this is your fault. It’s not you “making it weird” by not wanting to be the free counselor of a much older guy. You’re not “being mean” by wanting to keep your coworker as “just” a work friend. If this ends up requiring you to block him on everything, you’re not “overreacting.” ”

      It is mature to show compassion and open-minded to consider one’s own responsibility to/for/by/with/at/about anything. Those traits are part of you and are admirable! However this kind of person seeks out and walks all over the compassion with the inappropriate behavior and then, when that behavior is called out, twists it all back onto YOU by counting on that open-mindedness to cause enough self-doubt that they can at least make you feel bad if not get to continue/escalate the inappropriate behavior. Don’t fall for it!

      Don’t fall for that “because you didn’t say something about this earlier, now you don’t have a right to say something ever” BS either.

    2. “femme-identifying or appearing individuals” hi, please stop the misogynistic assumptions that butch lesbians are somehow exempt from the coercion to perform this kind of emotional labour for me. femininity and womanhood are not essentially linked.

      1. Thank you for saying this. As I’ve gotten more butch, the harassment has gotten, if anything, more scary; it’s really disorienting to see butchness conflated with somehow opting out of sexism

      2. But Somniorum specifically didn’t say this only ever happens to femmes? They said “It’s depressingly common for older dudes to do this to folks who are younger and of marginalized gender” before saying anything about feminine individuals in particular.

      3. I agree with your remark that butch women are NOT immune – hello, we’re frigging women and are thereby obviously just there to service certain types of men. And butch women are very much like any woman in our propensity to perform more emotional labour than men (ON AVERAGE – some of us don’t; plenty of men do).

        But it’s also true that young, cute/attractive, submissive-seeming, femme-type people are much more targeted for this kind of thing than we are. The more of those criteria you meet, the more, sadly, you get targeted by emotional vampires and outright predators.

        It’s good to acknowledge that we are not immune from this bullshit, but we also have a certain degree of relative advantage. Like anything intersectional, though, it’d be nice for anyone not to be oppressed/targeted just because they meet some “vulnerability criterion” in some effed-up people’s minds.

        1. NO, Leemac, that is NOT true, and it is in fact a lesbophobic myth that is used to obfuscate the very real and incredibly common targeting of butch and lesbian women (and! girls!) for retaliatory sexual harassment, abuse, and rape. If you didn’t experience it, great, I’m sincerely glad for you, but what you’re saying right now is not accurate and incredibly harmful. Femme is not and should not ever be used as a more inclusive synonym for woman, and women, especially including lesbians, who don’t fit into conventional feminity do NOT have any level of protection or “relative advantage” in the context of violent sexualized misogyny.

      4. I’m not somniorum so I could be off base here, but I thought they meant femme as an opposite to masc rather than femme as an opposite to butch. I read it as being inclusive of feminine/female-aligned nonbinary people rather than exclusive of butch women. Sometimes the language around gender can be ambiguous.

        1. Like, femme/masc vs. femme/non-feminine is only ambiguous in the worst possible way. I’m sorry, but that dichotomy is in no way less regressive or ultimately homophobic? I’m sorry, but this has been a pretty ill timed week to watch a bunch of allies n advocates cop to some incredibly simplistic and regressive ideas about what makes an oppressed class under patriarchy.

          1. To be perfectly clear, when I talk about a femme/masc spectrum I’m specifically talking about gender identity. As in, femme would encompass anyone who identifies as a woman AND ALSO anyone who identifies as nonbinary/another gender but sometimes or to some degree also identifies as female, femme, feminine, or otherwise woman aligned. Butch women, masculine women, gnc women, and both cis and trans women would all be already included by virtue of being women. The term femme sometimes gets used this way when someone is trying to emphasize and be inclusive of all the different ways someone might identify with womanhood. I’m also aware of its connotation of hyper feminity and it’s use as a specific identity. This is why I said it could be ambiguous. You can argue about whether it’s a good term for any of these things or not but the usage exists.

            In other words, when somniorum said “It’s depressingly common for older dudes to do this to folks who are younger and of marginalized gender. They especially love to do this to femme-identifying or -appearing individuals.” my interpretation was:

            “It’s depressingly common for older dudes to do this to folks who are younger and not men (either women or nonbinary). They especially love to do this to femme-identifying (ie, people who identify as women or as nonbinary but aligned with womanhood to some degree) or -appearing (ie, people who present in a feminine way or who could be read as women by the predatory older men in question) individuals. ”

            I realise that my context as a femme nonbinary person (that is to say, a nb person who identifies to some extent with womanhood; I’m not particularly femme by “femininity” standards) means that I was bringing some pretty specific ideas to my reading of it, but regardless, that’s how I interpreted it. I can definitely understand how people got the other reading, the implication that mainly feminine women are targeted by men in this way, and I found the insights of those who read it that way valuable. I just wanted to offer this alternative perspective. I see that somniorum has apologised below so I won’t be rehashing this question further.

            I’m sympathetic to your difficult week but no one on this thread made any claims about who can or can’t be considered an oppressed class. Even taking the least generous interpretation possible, we’re only talking about one very specific way of experiencing misogyny, not whether or not women who aren’t femme can experience misogyny at all.

          2. This is a response to you, Allya – I know that “femme” is sometimes used to encompass “anyone who identifies as a woman AND ALSO anyone who identifies as nonbinary/another gender but sometimes or to some degree also identifies as female, femme, feminine, or otherwise woman aligned.”

            I am pointing out that this is terrible. It is regressive, homophobic, and in fact transphobic. Like it or not, that term does not actually function as a more-inclusive synonym for “woman and woman-aligned people.” It functions to promote the idea that femininity is more central to the concept of womanhood, and thus to reinscribe the association of womanhood with femininity and as well to alienate some women and forms of womanhood from the class of women under patriarchy. It strongly implies that to be butch, masculine, gnc, or simply non-feminine is to be less associated or aligned with womanhood. Its double use as a word that means “anyone who identifies as a woman AND ALSO anyone who identifies as nonbinary/another gender but sometimes or to some degree also identifies as female, femme, feminine, or otherwise woman aligned” AND “people who identify as/with femme lesbian, nonbinary femme, queer femme etc. etc.” EXACERBATES this problem. This slipperiness simply allows people to simultaneously define “femme” as “woman” and “feminine” with LESS transparency and consequent awareness regarding the assumptions they’re making.

            On top of the basic premise that womanhood is aligned with femininity in an essential way, and the basic sense of masc/femme and man/woman (or male-aligned/female-aligned) as pinned spectra that can be shorthanded each for the other, this “femme = woman+” usage also strongly implies that butch and gnc gender presentation and identity can safely be aligned with conventional masculinity as performed by straight cisgender men. This is also a hugely regressive, homophobic, effectively transphobic idea that works to obfuscate some salient truths about what it actually means to be a butch dyke, i.e. it’s not really comparable to being a straight cisgender dude.

            The use of “femme” and corresponding posited categories of non-“femme” is frighteningly similar to the way that transmisogynistic radfems talk about the “privilege” of AMAB status for people who are men and people who are not men but women. It creates – and accords a specific set of privileges to – a class of “mascs” or non-“femme” people that includes both masculine men and masculine women. It divorces gender expression from its context within cisheteropatriarchy and then tries to encompass deep thoughts about sexism, homophobia, and transphobia. And again, the way that “femme” means “woman +” and also “femininity” makes this worse. Can you imagine anyone seriously trying to broaden the meaning of “butch” in the same way? There’s a reason for that unevenness. The versatility of femme is facilitated by unexamined essentialism – it’s just an essentialism of gender expression instead of the ones we’re maybe more sensitive towards.

            And if you need evidence of how badly this all works in practice, you can see examples in this thread of women either accidentally or intentionally asserting that to be “masc,” or non-“femme,” even if you are not a man but a woman, means that you are less likely to experience sexual harassment, violence, or assault, less likely in some ways to be seen as vulnerably a woman under patriarchy. This elision is not accidental – it is the direct consequence of the assertion that “femme” can function as a more inclusive synonym for “woman +” and all that other stuff we simply associate with womanhood and/or categorize as femininity. And while I appreciate the necessity of more-inclusive terms, I think maybe you ought to consider whether the inclusivity is actually happening.

          3. piny1, thanks for expressing that so well, it’s an educational read (and re-read) for me.

          1. piny1 – Wow! That was really educational. Thank you for explaining it so well.

            I think English is currently lacking in terms for the variety of sexual/gender permutations (if that’s the right word; I’m kind of blanking here), but I think that in 100 years or less, we’ll have it sorted. As long as people who really know and understand the issues work to educate the masses, the language WILL evolve, as it has done through the centuries. English is problematic, but one advantage it has is its ability to evolve.

      5. I expect we all get variations of the same nonsense, in slightly different flavors depending on how our gender presentation is received by the jerk du jour. Dear sisters and siblings, we are not in competition with each other in victimhood.

        1. On the one hand this is blandly true, but on the other hand it skirts a big component of sexual violence as it plays out in real life: namely that it is an expression of disparate power and autonomy created by inequality. Claiming that “mascs” or “butches” or “women who are not femmes” according to whatever sexist definition of that categorically sexist term you are using don’t face misogynist sexualized violence isn’t only misguided as to the real condition of some women – it’s a denial of some very pertinent forms of inequality, namely homophobia, misogyny, and transphobia (although none of the people using this oh-so-progressive concept masc/femme map ever seem to consider how it might apply to, say, a butch trans woman, which I think is significant).

          These specific forms of harassment are not merely varying flavors of the same basic idea. They correspond to differences in status. Being or being perceived as not-straight is a specific marginalized status, a specifically despised and vulnerable condition, and sexual violence doled out to women whose gender presentation marks them as not-straight is intimately related to that status. That’s one reason nobody wants to hear about it. It’s also why it is so enraging when people who consider themselves LGBTQ+ allies create these categories that lump gay women and gnc women in with straight men. No woman is exempt from misogynist sexual violence. Some women are shielded from, and thus dismissive of, homophobic and transphobic sexual violence. Some women, e.g. some straight and conventionally-feminine women, cannot intuit the massive problem with femme = women, because they themselves harbor a bunch of homophobic and transphobic ideas about what women are and are not.

          It is particularly enraging because this entire country has just held a national seminar on the real dynamics of sexual violence – contempt and impunity – and now more than ever, we have reason to get it. The LW did not write in about a man who sees a cute femme person and goes boner target identified. She wrote in about a man who knows that young women often cannot say no. Just based on her response to his harassment as described in her letter, he is right that he has a certain level of power over her. Her femininity is not the condition that is causing him to make that judgment about their relative status.

          When you assert that “mascs” or “non-femmes” are alienated from womanhood by virtue of their failure to fit within conventional norms for womanhood, you obfuscate the real mechanics of disparate power and thus the actual dynamics of sexual violence. We should not do that. And if our glossary is causing us to do that, we need to get some better words right away!

          And like I’m aware that this is a derail, but speaking as someone who has experienced similar harassment to the LW for being a butch dyke, I feel like I should be able to get through an entire comments thread about sexual harassment without encountering the implication or straight-up assertion that butch dykes are exempt or that homophobia itself is not intimately related to sexual violence and entitlement. Both assertions are damaging and rest on premises that frankly belong to the pro-rape side of the fight.

          All that having been said, commenters were not arguing whether all women faced misogynist sexual violence. One commenter made the implicitly homophobic (and transphobic!) claim that womanhood = femmeness broadly defined, and asserted that femme people are more likely to be singled out for sexual violence. Then some people who know better, i.e. women whose situated knowledge proves that sexualized violence is by no means reserved for “femme” (and lbr: this term functions to elide ‘woman’ and ‘feminine,’ and is not a term that gnc women typically prefer), took issue with that. Because hey, they just witnessed someone strongly implying that they are misogyny-exempt by virtue of being ungirly, and as so many of us have been bleakly repeating this news cycle, it’s 2017.

      6. Hello, I made a longer post at the bottom of this thread, but wanted you to know that I read this, and am deeply sorry. I was trying to only speak of my own experiences and observations, not minimize those of people who do not identify as femme or in the femme-masc spectrum at all.

        It was thoughtless of me, and I will strive to use less clumsy language in the future.

        Thank you for enlightening me on this, I very clearly needed it.

    3. **Such gross men like to make it about “maturity” while not even remotely seeing the hypocrisy. “Sure dude, I’m not mature for my age. Cool. So go find somebody your own age to bounce this off of.”**


    4. Hello, all! I wanted to apologize for my thoughtlessness. I was trying to speak to my own femme-identifying experiences in that I had noticed this sort of thing occuring with similar-identifying individuals. I was trying to be broader by using “marginalized gender” but I clearly failed.

      I acknowledge that those who do not identify as femme (or on the femme-masc spectrum, period) are also mistreated, harassed, and abused by older cisgender men. I was honestly not trying to imply or state otherwise, but clearly my wording was very clumsy.

      I am so sorry for this, and will be more careful with my words in the future.

      Thank you for the call-out, even fellow queers need this every now and again. I really do appreciate the patient walkthrough of why what I wrote was not okay.

  6. “my wife doesn’t understand me, not like you”

    It’s sickening how often I’ve come across this pity-party line (and fell for it once). It is absolutely used to zero in on those with sympathetic ears and groom them for future abuse. I wish I had read this advice when I was younger, much more naive, and often “too nice” to push back. This guy is a predator.

  7. “my wife doesn’t understand me, not like you”

    It’s sickening how often I’ve come across this pity-party line (and fell for it once). It is absolutely used to zero in on those with sympathetic ears and groom them for future abuse. I wish I had read this advice when I was younger, much more naive, and often “too nice” to push back. This guy is a predator.

    1. Seriously. The only correct response to that is “Really? I, a 22-year-old coworker who has only known you for a total of 400 hours, know you better than the person you promised to share your life with? Gross, dude, lose my number.”

        1. It’s like when my teenage students say, “You don’t get it, math is just so pointless and I’m never going to need it!” as though I couldn’t possibly grasp “I don’t like doing things I think are boring”. Only I’m actually sympathetic to someone who’s acting in an age-commensurate fashion whom I’m being paid to help.

          1. Off topic, but I very nearly wrote to my old maths teacher to thank her when, at 30-some, I found myself doing simultaneous equations to work out how big a corner wardrobe I could build in a specific space.

            She taught me that at about 13-14, IIRC, and I remembered how it worked over 10 years later. Also, I didn’t even know they had a real world application when I learned them. Go Mrs Dorling.


          2. Heather Bayly – See, now that’s the sort of “word problem” math teachers should give.

            “Using the following data, determine furniture placement in your studio apartment.”

            Also, “Using the following data, determine how much you can actually afford to pay for housing.”

    2. Yeah, I’ve had this sickening dynamic with a former boss. Every morning he’d come into my office, close the door and monologue. It started out with going over work stuff…fine…but then would segue into, “my wife doesn’t understand me,” and “today I got a ten-page letter from my wife about all the ways that I suck,” and, “I’d get divorced if it wasn’t for the kids but then my wife would get everything.” It was horrible. I’d break in on the monologue to remind him that, “actually I’m in the middle of that urgent proposal, why don’t we circle back later when I’m finished with it,” or “I really need to be checking in on the progress of X project” and he’d start sulking and threatening my job. He owned the company so I had zero recourse. Eventually I made a pact with a few other (female) employees that whenever they saw him cloistered in my office, they’d call me with an “urgent” question. There was always this underlying current of desperation, like he was this awful, unhappy man trapped in an awful life and I was the person he viewed as his life raft. It felt so gross, I felt so trapped and I AM SO FUCKING GLAD I DON’T WORK THERE ANYMORE.

      1. My go to response for any kind of dude spewing relationship woes at me is “whoa, I am NOT the right person to share that with. I am not okay hearing about your relationship.”

        Depending on the context, I may add in some hostility in my voice or body language to let them know that in zero way is okay. Once I added in “are you fucking kidding me right now? I am NOT your best friend and I will NOT listen to this.”

        1. The part where he was my boss, and he was threatening my job if I didn’t listen to his litany of woes, made that kind of tough. For sure it was a giant FIND A NEW JOB sign staring at me from space.

          1. Yeah, I dunno, some people seem to forget that we have bills and rent/mortgages to pay? That’s nice in an ideal world that people feel that they can mouth off to their boss who happens to own the company.

            For others of us, though, we literally have no-one to turn to financial help, we don’t have rich or even “comfortable” parents, we might be in debt, or, frankly, we’d never WANT to ask for financial help from friends/family. (While I grew up quite poor, I have literally never borrowed money off friends or family – and it’s something I feel very strongly about.)

            So doing something quite-literally job-endangering is something you only resort to if it’s truly untenable (say, the dude starts abusing YOU), or you’ve finally got your exit strategy lined up. That doesn’t mean that you’re a doormat and don’t speak up at all, but there’s such a thing as “career-endangering remarks” and knowing when not to make them (and start that exit strategy going).

          2. @Leemac

            Thank you. This was where I was at when I had that job. It was one of the hardest things to wrap my head around when I joined the work force – that we are/were STILL living in a world where men could do these things and much, much worse, and get away with it. It’s rife in my line of work, where small companies largely helmed by men are the norm – they’re so often dysfunctional little fiefdoms where the boss can do anything he wants, including wreck your reputation if you report harassment or reject his advances. But my friends in larger corporations didn’t fare much better when their bosses mauled them in locked cars on the way back from meetings or offered them promotions only in exchange for sex. If no one else wants to come forward as a witness, or if there are no witnesses, it devolves into a he-said-she-said situation and in most of the cases I’ve seen, the woman in the less powerful role always comes out the loser.

            The fact that people need their jobs, and oh, by the way, even if you quit that shitty old boss or coworker can STILL destroy your professional reputation with a few well-placed phone calls, is exactly how Harvey Weinstein got away with this shit for the past twenty-plus years.

      2. “You’re the only one I can talk to about this” is SUCH a red flag, even if there aren’t any other creepy dynamics (like age, gender, workplace, relative rank).

        Personal story: my now-partner felt trapped in a miserable relationship with someone who turned out to be massively abusive.
        Them: [increasingly horrifying details]
        Me, appalled: “…Who do you have to talk to about this?”
        Them, matter-of-factly: “Nobody. Well, you, now.”
        Me: “!!! Okay. I know for a fact that we have four mutual friends that would be safe to confide in. Let’s get communication started here.”

        We might not be even friends anymore if I had been their sole source of emotional support through the process of getting them extracted. And we didn’t have many confounding factors, particularly neither the age not workplace factors.

        1. Yeah, this is always such a red flag (except where, as in your case, the reason for not talking to others about it is a genuine semi-rational safety fear, as in “I’m afraid of my abuser and wasn’t sure who to turn to, thanks for the additional safe resources,” fear, not “you’re the only one I can talk to about how I hate my wife for being fat because I’m scared that other people will think I’m a bad person” fear.)

          I’ve encountered “only one”itis exactly three times. One was a depressed high-schools boy who dominated my previously healthy and diverse social life by making threats of suicide that I was the only one he could talk to about, also he might date me, also he didn’t want to date me now, though? Also how can he date my best female friend? He’s so depressed, he needs my advice RIGHT NOW AT 2AM about the friend because thinking about her not liking him makes him want to die, and I’m the only one who can help with his depression. Eventually he got into said friend’s pants and magically she was now the only person he could talk to, he was just so depressed, if she left he would kill himself.

          The second was a guy I dated for 9 months who would alternate between telling me he loved me, telling me about how he wished he could date other women, and telling me I was the only person who understood how upsetting it was for him that all women worth dating were uninterested in him. We broken up (his call, man was I dumb), shockingly, but the dynamic remained the same, other than the newly added addition of him talking about how upset he was that I was dating someone not-him because I was the only person who understood him and iIwas so insensitive to that since now I wouldn’t be available 24/7 (like, he actually came out and said it), but then also telling me how much he didn’t want to date me whenever boyfriend of the season got fed up with him calling at 2am and me tolerating it. We are… Not friends now.

          The third case is my best friend. She was raped by a man in her social group a few years ago, and nobody was mad at him/they kept telling her she shouldn’t have done [x]. Her boyfriend at the time was… Unhelpful. She was on a shitty HMO that has since been sued for refusing to send people to therapy. We have a weird best friendship in that we have no other friends in common, so I REALLY WAS the only person she could talk to because she couldn’t get medical care and all of her other friends were unsafe. She would occasionally express how much it sucked that she couldn’t talk to anyone but me.

          …and, like your partner, when I said “yeah that’s not okay for me or for you, let’s work on getting you new friends and to therapy,” she actually, like, got some new friends, called hotlines, and, like, changed that situation.

          LW’s creep is definitely guy 1 or guy 2. He says “you’re the only person I can talk to” and thinks that’s evidence that he has found a partial solution to the problem he’s complaining about, and now that he has identified you as a sufficient resource he can move on to the steps after “finding a support network” (and that if you stop talking to him he’ll lose progress on the problem). My bestie or your partner says “you’re the only person I can talk to” as (one of the many bits of) prima facie evidence that the problem is not yet solved, and that they’re not even close to completing the first step of identifying resources that will enable them to proceed to steps 2+.

        2. Um, I’m sure that this will get caught in moderation, but I should have included a cw for sexual assault/societal mistreatment of accusers.

      3. When I was trapped in an open office with coworkers who were perfectly happy to stand at my desk and talk at me for what seemed like decades (and I was not alone in suffering these prodigious chatters), some of us worked out a Skype signal that meant “I need a rescue NOW.” Would have been easier if my really cool boss had used Skype, because she would have come shut that shit DOWN, but she didn’t like the program and never had it open.

      4. Oh, man, I’ve been there, only it was a female boss, who was incredibly unstable. For reasons only my CEO understood, she assigned to be my interim department chief when my (lovely, agreeable, stable) department chief had a medical crisis. This woman would take hours-long, yes HOURS, long “meditation breaks” in my office. And she used that time to endlessly monologue about the dramas and woes of her life, and I was expected to respond with supportive commentary. If said anything about pending projects or work I needed to do, she would tell me that this was part of my “other duties as assigned” and reminded me that my annual review was coming up. The final straw was when she sent me a reprimand because a long-term project was not on track for completion on time. I went to the person one step above her in the organizational chain and showed him the reprimand ad a log of all of her “breaks” in my office, including time stamps and the topics discussed. (Mostly vague terms like, “relationship problems,” “credit card debt.” or “her cats are being distant.”) He was horrified and the reprimand was removed from my work file. Interim department chief was brought in for some sort of HR attitude readjustment and was very cold towards me until my beloved boss got out of the hospital.

        The power imbalance and the way I felt cornered made me so RAGE-Y. Who the hell continues a conversation with someone who is clearly unwilling? Who feels OK spewing out their life’s dramas, knowing that the other person doesn’t care and is actively looking for ways out of the conversation?

    3. Yes!! In general, I’m wary of people telling me I’m special in any kind of over-the-top way. “You’re the only one I can talk to,” “you’re the only one who gets it,” “you really understand me (unlike ____ person who should understand me but doesn’t),” “I don’t know what I’d do without you,” etc.

      It’s just too easy for any and all of these to turn into emotional manipulation and pressure for me to continue doing whatever it is they want, even if it doesn’t work for me. I like being able to support and help out my loved ones, but for that to work, I need to know that they’ll understand and have other resources when I’m not available. I’m not anyone’s automatic love-and-attention dispenser.

      1. You know, I’ve tried to be judicious about not using “I don’t know what I’d do without you” with my husband because I don’t want him to feel like I’ll collapse if he ever becomes unhappy in the relationship and needs out (unlikely but shit happens), but I haven’t watched my use of that in friendships and definitely sometimes say it when receiving emotional support. Thanks for listing it; I can recall times that I’ve used the phrase intending to express my serious awe that someone has really gone above and beyond what they could reasonably have been expected to do to help me with a difficult problem, but I hadn’t really thought about how it could be received. Especially since I use it when I’ve encountered a problem that’s urgent and will cause me a lot of bad consequences if not solved, I’ve probably used it in ways that make it sound like I want the listener to know how reliant on them I was/am and how bad it will be if they don’t provide similar assistance next time.

        Doesn’t it suck to find a new way you’re still an asshole? 😉

        1. Don’t feel bad, it doesn’t suck that you are willing to learn! We are not born with all this we learn by living and experiencing. The only reason I stopped using it ( over 20 yrs ago) was bc it was used on me by my ex who ended up being a horrid predator who used it in beginning as a hook. I thought it was a sweet declaration of his love before things went south and he used it to justify why I was ruining his life by wanting out. We live and learn. You’re ok.

        2. Well, “I don’t know what I’d do without you” is often a generic expression of appreciation. I’ve had it used that way TO me, and I’ve used it as well. It hasn’t seemed oppressive, because actually it’s quite clear that the person CAN “do without” me, and has, and is going to tomorrow.

          So just as an expression, I don’t know that you have to censor yourself too much. But words do have meaning, and if it starts popping up often in one relationship, it might be a cue to you to make sure you DO know what you’d do without someone, even if you have no plans to ever be so.

        3. Maybe change the tense? “I don’t know what I would have done without you,” is specific to a particular event/situation, and less likely to seem like you are hanging all your hopes on that one person, forever.

          Also, you can say, “Wow! You really went above and beyond here!” to express your gratitude, and again, it’s specific to the particular event/situation, and less likely to seem like you’re grooming them for permanent sounding-board status.

          I think you’re OK.

  8. LW, I don’t have anything to add to the good Captain’s excellent advice, I just want to offer moral support. Your instincts about this guy are correct, so keep standing in your truth and hold those boundaries. This line in your letter: “I want to maintain our good working relationship”. Of course you do, because you’re kind person who cares about holding up your end of the social contract. Alas, this is what the guy is exploiting and manipulating here. When I was in a similar situation, someone gave me a way to think about it that really helped (and might help you). That framework was: “The guy is not worried about maintaining your good [work/school/friend/etc] relationship. No matter what he says, if he cared about maintaining that, he would not be acting this way. You don’t have to tie yourself in knots to maintain a pleasant vibe with someone who demonstrates that they don’t care.” It freed me to not care so much about whether my reactions would ‘disrupt’ a dynamic that – he – was already disrupting.

  9. A friendship where you can’t state a boundary without retaliation or “ruining the friendship” was never a friendship.

    This can never be said often enough. Thanks, Cap.

    1. Yup. I remember my abusive mother insisting I do some stupid thing, me saying No, and her whining that if I loved her I would do it. My reply to her was this: If you love me you wouldn’t ask me to do that in the first place. Followed by another No.

      Emotional manipulators depend upon you caring more about “being nice” and putting their needs above your own to get what they want, which usually includes you being OK with major boundary crossing.

      Don’t fall for it. Friends don’t treat you like emotional dumping grounds. Friends don’t use you like you’re a thing rather than a person with your own wants and needs and emotions. This guy is not your friend. He’s a manipulative emotional vampire.

      Shut him down, hard, and cut him out of your life.

  10. Dear LW,

    I think this guy wants to have sex with you. Even if he doesn’t, he’s wildly inappropriate.

    Work friends don’t call at 2am.

    Well intentioned people don’t ask their work subordinates for personal comfort.

    Middle aged straight men with no agenda don’t push for intimacy with very young women.

    This guy is not a good guy.

    Extricate yourself as much as possible.

    Jedi hugs if you want them.

    1. “Middle aged straight men with no agenda don’t push for intimacy with very young women.”

      I’ve had some middle aged gay guys buddy up to me in college. One in particular was very lonely and was always willing to listen to my problems and tell me how great I was. In hindsight, I have no idea why they did this or why I let them get so close to me when I barely knew them. I think some older people know that women in their early to mid 20’s are basically “free friends” because most of them haven’t been empowered to set boundaries yet.

      1. This! An older, experienced woman is much more likely to set strong boundaries and less likely to be cowed by “but I thought you’d be different,” “I’m just in a lot of pain right now, and you seemed like a caring person…guess you’re not,” etc. Predatory men know this and zero in on young women because of it.

      2. “I think some older people know that women in their early to mid 20’s are basically “free friends” because most of them haven’t been empowered to set boundaries yet”

        Wow, I never thought about it that way but…yeah.

        *wishing fervently that I could redo my 20s*

      3. “I think some older people know that women in their early to mid 20’s are basically “free friends” because most of them haven’t been empowered to set boundaries yet.” oh jeez I think you just explained a lot of Weird Shit that happened to me in my early 20s

    2. Yep, I think he’s hoping the 2am calls will turn into phone sex/sext or a booty call. But I can be cynical…

    3. Yup. I mean, I suppose it’s possible he’s just into like weird power games about getting younger women to sooth him like a mommy (JESUS), but the chance that he’s not at least hoping in some fantasy way for sex is vanishingly small. The idea he’s just looking for a “friendly ear.” Sweetheart, I’m sorry but no he’s hoping he can wear you down and somehow maybe you or one of your even younger friends will throw him some pity sex. If he wanted a friendly ear he wouldn’t be fixating on romance, pushing your boundaries, ignoring your pushback, etc. He’d more plausibly be talking about non-romantic problems he has. He’s being super creepy. And it’s 100% ok to feel that. It’s his problem to stop acting like a disturbing creep and clean up his own mess. You get to judge his actions. Treat with extreme caution.

    4. This was basically my thought. When he texts at 2 am he is hoping for a booty call, not commiseration. I hate guys like this who say some vague creepy stuff and expect the object of their creepiness to..what? Read between the lines and jump on their dick with plausible deniability? If you want to get with someone fucking ask them out.

    5. My closest friend is a guy, he’s great to bounce these kinds of scenarios off off…according to him, it’s pretty much always about sex…

  11. OOOH this. So much this! All of it. I have had some wonderful supportive friends 20 years old. Even men. The good ones felt like uncles. The level of emotional labor and reciprocity was equal. They would defend me to the death. They never messaged me at odd hours. But that is definitely the rare exception.

    I have had soooo many more “relationships” with much older men and the power imbalance and let’s talk about the one older married retired guy who was sub-letting part of my boss’s studio and we became friends chatting about world-travel until that one time he showed up at 10 pm on a night he knew I’d be there late at work to split a bottle of wine with just me because I looked “down” earlier (because my Grandpa was dying btw). And he told me of his relationship troubles. And all the embarrassing “confessions” he loved telling me. About how he came in to my place of work a few days later in the middle of the day to confess his “feelings” for me. But also to tell me he loved me like one of his “nieces” and didn’t want to try and have sex with me or anything. And how he stalked me after I told him to leave me alone because the cumulative effect of “weird” moments hit critical and I needed him to not (tw for the creepiest stalkery moment) [tw]get drunk in dark rooms alone lying to his wife about where he was while watching me drink with friends out in the courtyard.[/tw]

    When his wife showed up, saw me outside in plain sight and asked where he was you better believe I told her. Drunkenly lurking alone with his booze. Apparently he was supposed to be home with her that night packing for a trip.

  12. I feel… weirdly uncomfortable about OP using apologetic/taking the blame language on this guy (e.g. “sorry I didn’t say this earlier” or “you’re right, I’m uptight”). Like… isn’t that still doing his emotional labor for him, painting yourself as the person who’s the problem in the situation? I feel like it’d be better to just skip the “I’m sorry” bit entirely, and if he made accusations, just brush right over them with “so we’re clear on the ‘no more 2am feelsdumps’, then?”

    1. Good point about the “sorry” – to be clear, “you’re right, I’m uptight!” is meant ONLY if he uses that word to manipulate, like, Jeez, you’re so uptight. “Sure thing, I AM really uptight! So, no more 2am messages? Cool!” Like, taking the thing they are using as an insult and claiming it as a badge of honor.

      1. Saying “you’re right, I’m uptight” also makes me smile in the same way that one of my favorite responses to accusations does:

        “Whatever helps you sleep at night.” Followed by a reinforcement of said boundary, of course.

        1. Makes a handy poem: “You’re right, I’m uptight. Whatever helps you sleep at night.” Kind of like “Good night, sleep tight, don’t let the bedbugs bite.”

        2. I’m also a big fan of just replying with “Okay.” “Wow you’re uptight!” “Okay.” They want me to defend myself and prove I’m not whatever they just accused me of? Sorry man, wrong store.

          1. Exactly!!! Just bc someone throws you a ball doesn’t mean you have to catch it. You can duck and watch it go by, continue on with life…

          2. I’ve seen someone go into a serious meltdown because of a well-timed “Okay”. For some reason, this person really, really wanted to fight, and the other party was beyond uninterested in doing so; it was like all that energy had nowhere to go and the first person had the human equivalent of a blue screen of death.

      2. Truly, that type of script is the single best piece of rhetorical and conversational judo I’ve ever learned anywhere, including from my therapist. I can’t thank you enough. Being able to breezily respond to manipulative accusations of my supposed shortcomings with “yep, I’m the worst, and I’m still not going to do the thing for you/let you do the thing to/with/around me!” is not only super effective, it’s *really* satisfying to watch someone flounder after you refuse to follow the usual “oh no let me prove I’m not [bad thing] by continuing to let you trample my boundaries” script they expected you to follow.

      3. This seriously is a great approach to people who are negging and manipulating. If you don’t want to agree (and agreeing really does suck all the wind out of their sails so consider it) you can also just stare at someone for a beat too long and then ignore the neg. Or respond with the flat “wow” or “gee that’s a weird thing to say, but anyway, I do need you to stop doing [thing]”. Arguing back is generally what they want, because they want you to try to prove you’re not whatever they’ve accused you of by doing the thing they want you to do.

        Also anyone who uses the “I thought you were more mature” tactic deserves to be immediately put into a quarantine rocket and fired into the sun because it’s specifically a tactic used by older people on young adults (or younger) and as far as I can see that’s always intensely skeevy from anyone who isn’t a parent trying to get their 3 year old to stop screaming in the supermarket. No one says this to 40 year olds. The horrendous implication is that you’re young enough to be desperate to be seen as “adult” and if someone is using that as leverage on your behaviour they’ve lifted up their human skin mask to reveal the lizard person underneath and you should avoid them at all costs.

        1. OMG your user name!!!!

          The whole point of a neg is to get the person being negged to play along with what the neg-generator wants. The only safe ways to avoid this are to either refuse to play entirely (leave/okay) or to agree with the neg.

          “You’re so beautiful! I could never date a girl like you, you’d be sure to leave me in a heartbeat.”
          “That is a very weird thing for you to say, but if that’s how you feel, I’m not going to tell you that your emotions are wrong.”
          (Online Dating Dude doubles down on the neg, I ignore and block)

          1. For this particular set-up, I think the reply is, “You’re right. You never could date a girl like me.” And then ignore/block.

            I love it when people hand me such excellent straight lines.

      4. My favorite dismiss of a neg is, “Whatever you say, bro. It’s your story, you get to tell it however you want to.”

        Usually followed by some version of, “It changes my mind not one bit. [Thing you want to happen] isn’t happening. And [thing I told you to stop] ends now. As long as you tell your story walking, dude, you have my full permission to write me as the evil super-villain.”

        The more of these jack-wagons who avoid me because they think I’m [insert neg here], the better my life is.

      5. Or even. “If you say so. You’re clear on the ‘no more 2a.m. messages”
        You’re not arguing with him, you’re just making clear you give zero fucks about whether he thinks you are uptight / unreasonable / whatever.
        I was also a little uncomfortable with using the ‘I’m sorry ‘ language or explicitly agreeing, although I’d agree that it’s possible to agree with someone in a tone of voice that makes it clear you are, in fact, not agreeing with them at all”

        1. “I’d agree that it’s possible to agree with someone in a tone of voice that makes it clear you are, in fact, not agreeing with them at all””

          There’s a wonderful scene in Jeeves and Wooster, where Bertie Wooster tells his valet, Jeeves that he has a particular way of saying, “Indeed, sir,” that implies that, were it not for his feudal spirit, he’d really be saying, “up yours.”

      6. “You’re so uptight!”

        “You’ve just validated my decision to distance myself from you. Thanks for clarifying everything and have a nice life.”

      7. All-purpose version: “That may be, but nonetheless [restate boundary].” Really, I love “that may be” as a way of evading distractions and sticking to the point.

    2. If LW wants to omit the ‘I’m sorry’ from the former, it still works; ‘Yep, I didn’t say this earlier, but I’m saying it now.’ FULL STOP. An actual friend would respect this; dude in question will likely start whining that it’s not fair of her to change the rules. Either response will be illuminating.

    3. I agree with you that it would be better. That said, I think for a lot of people setting boundaries can be difficult, and sometimes those ‘softening’ words can help them get started.

      It’s not perfect (and of course it leaves more room for pushback) but it can sometimes make the obstacle of “rudeness” easier to master. (Particularly one where there might be an imbalance of power, like in a work situation.)

      *to be clear, I don’t think setting boundaries is rude, but a lot of us have been socialized so that it can feel that way.

    4. I use that a lot at work, when customers get precious about me telling them the rules. “Yep, I’m strict! Yup, I’m uptight! Yep, I’m mean! Now put your phone away please!” Works a treat. Thanks, Cap’n.

    5. Yes to this! No apology! Agreeing with ‘yep I’m uptight’ isn’t taking the blame, I saw it as well placed snarkytimes. A way to shut down his ‘typecasting’ where he expects her to do what he wants or else she’s the bad thing he called her. See Gavin de Beckers gift of fear. Good for all sorts of dysfunctional wieners not just the violent ones

  13. I’ll bet the reason he’s venting to a younger woman is because he either drove away his same-aged friends with this, or he still has friends but they’re mature enough to tell him he needs to stop unloading on them, so he’s clinging to younger women – he thinks they’re naive enough not to know he’s overstepping, and they’re female, they’re supposedly super open and approachable and have an endless capacity for emotional labor (not).

    I’ve been the friend who shared too much heartbreak, and sometimes people told me to stop and other times they should just ignore those messages or change the subject. At 28, I know better now, and I’m very careful not to dump too much and to show appreciation when someone does become a sounding board for my woe. At Peter’s age, he should definitely know better, but either he doesn’t know better or as I suggested above, he’s seeking out people who don’t yet know his behavior is selfish, so LW should definitely shut it down now.

    1. People like this man pick their victims because they are more likely to get away with their bad behavior due to the target’s inexperience. It’s predation, not appreciation. The sooner you show them that you don’t have to tolerate it, and in fact will not, the sooner they will move along to find one who will.

      1. Yep.

        You don’t call people at 2am and talk about Lurve and Feelings and Romance to a person you do not want to touch naughty bits with.

  14. You don’t have to, but if you’re intent on parrying/defusing, developing a sudden wacky obsession as to the cause of his problems (eg. onions or green paint), and continuously harping on it, can show up how ridiculous it is. So you: “well, of course she left you, you didn’t buy her onions often enough” and then everything he says gets flippant response working onions in. Meta-level objections “I want you to take me seriously” etc. get, “free advice, worth what you pay for it! [more about curative powers of onions for relationship woes, recommendation for onion poultices].”

    Goal is to make it 100% predictable – onions is the only thing you’ll ever talk about after midnight.

    Part of the problem is that because talking to you has sometimes gotten him sympathy, and sometimes gotten silence, is that when you stop, he’s having an extinction burst – he thinks implicitly that his 101th message might get the feedback he wants. Getting predictable, but useless feedback limits his spiral – he’s less likely to keep talking, because he’s not living in hope that this time you might reply.

    1. This is hilarious and could be a super fun way to mess with creepos in general. Thank you for the laugh! With this particular creepo I wonder if might run it through his internal filter that only sees what he wants to see and take it as flirting though?

    2. I agree with jennthemighty – the play is superb, but I think it requires an indifference / calm on the part of LW that she does not currently feel. As long as an interaction with this human-shaped bodily orifice for waste disposal causes even an ounce of anxiety to LW, I think it’s better to cut the whole thing off.

  15. “I think he is just looking for a friendly ear”

    I bet these are his own words. Funny how that ear just happens to be connected to a young female subordinate.

    1. Ooooh, yes! What a coinkydink.
      Gotta love those young, girly ears. The quality of the listening done with those must be unmatched.

      1. Never mind that the ears attached to a trained and paid counselor come with a professional level of advice…

        1. Yes, but he has to pay for access to those ears. Younger female subordinate ears come free – or he can imply that the listening is a job requirement (as per Guava upstream) and failure will result in unemployment. Plus a counsellor will tend to cut through the self-protecting bullshit filters he’s thrown up, and point out how he needs to change a pattern of behaviour he’s actually found thoroughly rewarding all these years. Which means he doesn’t get attractive young women paying attention to him any more, which upsets his boner.

    2. Yep. Sure, he’s definitely looking for a ‘friendly ear’ to talk through his feelings. Which is why he’s talking to…a work colleague??? Wait, that doesn’t follow.

      I’m pretty sure what he’s actually looking for is an ear attached to a body he finds attractive and a person who he thinks won’t know how to turn him down.

  16. Yeah, his behavior is weird and way too personal. In your shoes, I’d feel totally justified just not even responding to him anymore and limiting his access to me on social media. If you aren’t ready to go that far, I think Captain’s scripts and seeing how he reacts is a fine first step. But yeah, if he keeps it up or responds badly, you don’t owe him any further contact. You said you wouldn’t talk about it with him anymore, so he shouldn’t be surprised when you don’t respond to him continuing to talk about it.

  17. Captain Awkward: Helping people everywhere fight negs. Good luck, LW. This guy is using his position of power and attempting to manipulate you. I hope you can fight his negs the way the Captain said and get him off your back.

  18. When I was a college student, i was working with an older woman who started oversharing personal difficulties with me. She was my boss. I didn’t know how to respond, so I listened and answered the best I could. A few weeks later she apologized to me because this was hugely inappropriate on her part.

    Differences: we were both straight women with no romantic potential & she quickly realized what she was doing is wrong.

    I share this story because now that I’m the older person working with younger people, I can see how this happens in all relationships and aspects, but it is never okay.

  19. THANK YOU, Captain! I have a real-life Peter (real name!) in my social media feed at this moment, and was just wondering how do I extricate myself from this. Slowly, I am extinguishing the unwanted behavior. And I suspect that he’s not happy at home with his wife/girlfriend (I don’t know the exact nature of their relationship — didn’t want to know, not my business). I do think he told me, but I deliberately forgot.

    This Peter and I knew each other tangentially at my college, long ago and in another state. I never took a course under him, but he was there, as a professor. This was fully 20 years ago! Maybe more! So out of the blue one of us added the other on social media (I like adding people I know, even tangentially, I’m interested in others’ lives and experiences but at a distance!), and then, the messages from him started coming, fast and furious. And I was like, um? Okay? Hello, tangential acquaintance I knew but never talked to! Why are you so interested in blowing up my chat box?

    And then the grooming started. Oh let’s discuss our writing — in text. Can I call? Can we text? What other apps do you have? Just NO. Sorry, dude, I don’t use WhatsApp or Google Hangouts, or this, or that, or the other. I only chat here on this platform and hey, I’m SUPER busy, lots to do in the real world.

    Maybe it’s because I’m a widow (ie suddenly single, “available”, haha no)? Maybe he’s more than likely unhappy in his relationship? Probably. I just know I made myself sound super busy, told him flat out that I just don’t get on the computer that often, and am not much of a chatter, and then just started replying minimally to his messages. It’s slowed down from a torrent to a gush to a trickle, now to a drop. And I’m cool with that. And if it stopped altogether, I’d be just fine.

    So, there are things you can do if you don’t want to engage, or extinguish unwanted behavior, or just not engage at all whatsoever. Do what suits you, and go on with yo’ bad self.

    1. I’m so sorry that happened to you. I hate that vulture move when they show up when you’re at your lowest.

  20. We need to send this letter and its answer to literally all women entering the workforce. Make it part of HR training.

    To men also, they need to see how their predatory behavior looks from the other side.

    1. I teach a college class on professional communication and I’m actually wondering if there’s a way I can work this into my curriculum somehow.

    2. And to men who AREN’T predatory, so they can understand that it exists, and what it looks like. And be prepared for how to handle it.

  21. “When I do respond, we get our wires crossed…”

    I mentally read this as “When I do respond, he twists my words and makes it sound like I’m doing everything wrong, and then we end up arguing about the way I argue instead of what I wanted to talk about in the first place.”

    I don’t know if this is what’s actually happening here, LW, but it has certainly happened to me more than once. I just don’t think it’s likely that the two of you are having a good-faith conversation and somehow you’re both having a hard time communicating – because it sounds to me like you’re communicating just fine. Certainly I had no trouble understanding you, and it looks like the Captain and the other commenters are understanding you just fine as well. What’s far more likely is that he sees you trying to set some boundaries, and he doesn’t like it, so he turns everything back on you and tries to make you the bad guy.

    In other words, *he* is crossing the wires, not you, and he’s doing it deliberately. This creepiness and supposed communication problems are all on him, every bit of it.

    1. I came here to say this! Nine out of ten dentists recognize this as a recommended gaslighting technique. To test: when the “wires are crossed,” is he *actually* apologetic? (“Oh sorry, my bad, I misunderstood you. I’ll stop now!”) Or is he accusatory/defensive? (“But you SAID you were interested in rice sculptures.”)

  22. Oh, LW, one of the things I wish I’d learned much earlier in life is that your friendship is a privilege, and this is doubly true in work spaces. What you are being paid for is turning up at the festival and doing festival-related things, and what this man has conned you into thinking he has bought from you is 2am attention and sympathy and catering to his happiness and and and…

    No! You don’t have to be friends with everyone who wants to be friends with you. And you certainly don’t have to be ‘friends’, where the ‘friendship’ is ‘they are sad and you comfort them’, and you certainly certainly don’t have to do either of those things with people just because sometimes you’re paid to be in their vicinity.

  23. #Lysistratatime #forreal. This fucking guy, AGAIN. LW, jedi hugs and all the anti-negging, dealing with HR if you go there mojo that you could possibly need. I also work daily with students 30 years my junior, I WOULD NEVER EVER EVER DO THIS, HE SHOULD BE FREAKING MORTIFIED OH MY MAUD REALLY. You are doing great figuring out a situation designed to make you feel off balance, you got this.

  24. Not a coincidence he’s split up with his girlfriend! I’ll bet she was the previous sympathetic ear, and now she’s grown tired of it.

  25. A couple of random thoughts:

    *I’d encourage you to save his text messages, emails, social media messages, etc. You don’t know yet how he will react when you try to enforce boundaries, but you can start documenting now in case he behaves badly.

    *Even if his behavior never leads to sexual harassment, he’s still abusing his seniority and power over you in order to make you feel like you must be his emotional dumping ground. That’s really gross behavior and you have every right to ignore his messages as much as you want (if that’s what you feel most comfortable doing).

    *People like this are emotional vampires who use others to fulfill their emotional needs. If you stop being useful to him (by soothing his feelings), he will probably stop talking to you. Ignoring his messages is a step in the right direction. When you can’t ignore him–such as when you have to talk about work stuff with him–be REALLY boring and don’t give him what he wants. Him: “Boohoo, poor me! I feel so sad!” You: “Okay, but going back to work-related thing…”

    *I like this script a lot: “I like working with you but this conversation is too personal for me.” It states your boundary while offering NO commentary on his behavior. Men like this don’t tend to respond well to criticism (in my experience, they lash out or whine about their poor little man feelings). I personally wouldn’t want to deal with that.

  26. My favorite way to deal with negging is the phrase “be that as it may.” Just respond to their neg with “Be that as it may, [restate original boundary.]” It acknowledges their point without getting into whether it’s true or not, and it gives you a nice segue back to the real issue.

      1. “OK, great, and…”
        “But enough about you, let’s talk about…”
        Or the time-honored, “Huh, I didn’t plan to be insulted today, but here we are.”

      2. Yup. There’s also the not-pology; a flat “I’m sorry to hear you feel that way” followed, as always, by [restate original boundary].

        It is, however, absolutely key not to confuse this with actual apologies. If you use this one, say it absolutely flatly, no apologeticness in your tone, and make sure you use that phrasing rather than phrasing it as an actual apology.

        1. Every time I hear that not-pology (love the word!), in my head, I hear it in the voice of Sarevok from Baldur’s Gate: “I’m sorry you feel that way, old man,” right before he kills the old man.

  27. To paraphrase Chump Lady, though she was talking more about cheaters trying to rope back in their exes, you are not obligated to deal with Peter being a sad sausage.

  28. I am concerned about the professional damage this guy can do to her in the meantime before the next festival, including but not limited to preventing her from working at the next one. What sort of things can she do, apart from just reporting to HR? Should she tell anyone and everyone about this?

    1. I think you’re in http://www.askamanager.org territory here, but I would be careful about telling this too widely – I think it would be viewed as unprofessional in many contexts. The answer here is so dependent on workplace culture, but usually the advice is to document everything, ask the offending party to knock it off clearly and in writing, and then if they don’t ask your manager and/HR how they would like you to proceed or if they can help you out. Sadly, the reality is that older guys are often protected by workplaces over their younger victims – they often have better social connections at work, or are harder to replace due to their skills and experience than a junior employee. And sometimes sexism and victim blaming happen no matter how you play it – a lot of workplaces (and people generally) will blame the person complaining for “creating drama” rather than the person they’re complaining about who’s the actual cause of the problem.

      So, really, my own advice would be document, ask him to knock it off in writing, if he doesn’t take it to official channels, initially with a “feeling it out and asking for advice” conversation and then a formal complaint if that goes well and it seems encouraging. But, all the while I would have low expectations and be looking for different work because unfair though it is these things often don’t go well. 😦

  29. Does your phone have a “quit time” setting. Many phones do let you define hours when you don’t get calls, texts and notifications. Usually you can add in exceptions (like people you have “favorited” in your contact list.) His late calls and messages will be so much easier to ignore if you don’t see them until the morning.

    In general, managing your availability can be golden. My list of people who can contact me after midnight is 4 persons long. Sometimes that means I miss drunk calls/texts. This makes me not at all sad.

    1. One of my best friends calls the favorites section the “list of people who can make [his] phone make noise” and it was a day of honor when he decided to add me to it.

  30. As a (recovering?) extreme-people-pleaser in my mid-30s, I have just (JUST) for the first time, unfriended someone on Facebook this week. It was a guy I dated a long time ago who was not cool, and who has always made me uncomfortable and who posted a weird #metoo thing and I was like, do I say something? And then finally, it dawned on me that…I could just make him go away (from my Facebook and therefore my life, since we never hang out IRL).

    I don’t know why it never occurred to me before, but I know I have this sense that I want everyone to get along, especially exes and for some reason my sense of well-being feels more complete when I can believe that everyone IS getting along. And the inside of my head has often sounded like you, LW (“I shouldn’t ignore him…” is something I literally texted a friend today about a different ex). But here’s the thing: you SHOULD (as others have rightly pointed out). And also, you CAN without being the Reason People Aren’t Getting Along.

    I know for me, it can be so hard to get past that guilty feeling (“I don’t want him to feel bad!”), but as someone who works with people who are 20 years younger than me (teenagers, but still), I can tell you with absolute certainty (as the Captain already has) that his behaviour is not cool at all. He should be the one offering mentorship and wisdom and demonstrating what healthy work boundaries look like to YOU.

    HE is going to be the Reason People Aren’t Getting Along if he raises a fuss about not having access to your sympathetic listening ear at all hours of the day. And it makes me VERY ANGRY that he seems to think this is something he is entitled to.

    /sporadic all caps

  31. “you are not a 24 hour emotional labor vending machine and that you get to say no to things” – o yea verily how I love this image. Would that I had had this column and community when I was young and self-care-boundary-challenged, I would’ve helped me repel the older men whose “wives didn’t understand them” or “just wanted to help me”. Oy.

  32. Another thing that stood out to me is the 2AM-ness of the 2AM messages.
    LW, is 2AM a normal time to be awake in your field? I realise you’re a student and “normal time” is variable with proximity to exams and projects, but still. 2AM is a rude time to expect a response without explicit prior agreement.
    I’m a freelancer with clients in many time zones, which means I get emails at all times, including my sleep hours that overlap with office hours in some of those time zones. Everybody understands that the overseas freelancers will answer next business day (and those that don’t, don’t stay my clients for long).

    This guy isn’t even in another timezone, he’s deliberately choosing to bug you in the middle of the night. SIDE. EYE. Polygonal eye even.

    There is 100% nothing weird about setting your phone to mute overnight (or claiming that you’ve started doing so) – a lot of people use their phones as alarm clocks these days and mute everything but the alarm so they can sleep without needing to worry about transatlantic tweets waking them up, much less “friends” , at 2AM.

    You could also mute his texts specifically when not working, and IF AND ONLY IF asked, say you’ve started muting your phone at night to sleep better/reduce study distractions/avoid waking the loud pet/because your roommate asked/something.

    1. Yes, totally! Like, even if EVERYTHING else was cool (which it is not), 2am is …. crazy. Nobody had better be texting me at 2am. I agree, there is 100% nothing weird about setting the phone to mute, or white-listing ONLY people who you’d want to txt you at 2am if there was an emergency. But this guy would not even make that list, yet he’s texting at 2am? NOOOOPE.

      1. Very fast true story–once a guy called me in the middle of the night, insisting that he’d loved me from afar for aeons and had to know how I felt about him RIGHT NOW. However, it was (as mentioned) the middle of the night, I was tired and groggy and grumpy. So rather than “who is this mysterious swain, and I swan, what do you mean you love little ol’me?”, he got this:

        “What the ACTUAL HELL, it is oh-dark-thirty, and no one who actually loves me would call me at this hour unless it was an emergency. If you know me so well and want to talk about your feelings, talk to me about them AT A REASONABLE HOUR. I’m going back to sleep now. Don’t call me back.”

        Still don’t know who he was, since he never bothered to tell me his name, and no acquaintances confessed love to me over the next several days.

        But LW, 2am FEELIINGSDUMPS are not your responsibility, even if he wants to make them so. Let him dump his rancid heap of feelings on the floor, and it is completely your decision whether to try to pick them up.

  33. LW, I have a boss who is a middle-aged straight man. We go for drinks together; he’s a mentor as well as a boss. He would 100% never, ever, ever do anything *remotely* close to this. He would be *horrified* at the very thought.

    Your boss is not acting the way a good, non-creepy man behaves. It doesn’t matter what his intentions are: his behaviour is weird, not okay, not something you – or anyone else – should put up with.

    The best of luck with employing the Captain’s scripts, and get some Team You onside as well if you can. Ask A Manager is also a great place to go to recalibrate your sense of what’s normal and not at work.

  34. I had a sudden, glorious vision of LW replying to the next one of Peter’s texts (I originally typed “tests,” and I think that works just as well): “Gee, Peter, I really don’t know how to help you with this. Why don’t you ask [Boss], he can guide you so much better than I can.” Stand back and behold Peter’s furious backpedaling!

    1. That would be fun to see.
      Alternately, for [Boss] insert [male coworker of same age as creeper] or better yet [coworker who is twice as old as creeper]. I think that would work regardless of older coworker’s gender. Creeper doesn’t want Old Woman Sympathy.

      1. God, I tried that once and the guy angrily asked “what’s he got to do with this?”

        Jeez, dude, for someone who claims to want to have X social norm explained to him in detail, you’re awfully picky about who does the explaining.

  35. One day I’d like to read a letter that says “Dear CA, I have a SO and we treat each other with kindness and respect. Our families and friends respect our boundaries and don’t try to manipulate us or make us feel guilty for living our lives in the way that makes us happy. We are respecting of others differences and with the current world situation world peace may soon be on the horizon (**a person can dream, right?). Anyway CA, on to my question? What TV series should I binge watch next?”

    LW, here’s hoping that you can get this guy Peter to back off and work towards my dream letter. 🙂

    1. Dear Captain Awkward, recently a friend crossed a line. I firmly restated my boundaries, and she accepted it gracefully, apologizing for her misstep. Any recommendations for good music?

    2. Dear Captain Awkward, my baby (literal human child of less than a year of age) wakes up an hour before the alarm, and my spouse takes the baby into the other room so I can sleep until the alarm. Any ideas how best to express my appreciation for my coparent?

  36. All of the Captain’s scripts are good. I have one more way to enforce boundaries while you’re applying the scripts: Put them on a schedule.

    Right now, he’s texts you in the middle of the night, and you answer at that hour? Decide, unilaterally, on a time schedule that works for you, maybe 2 in the afternoon on Mondays and Thursdays. He texts you, calls when you ignore the texts, and generally runs around waving flags trying to get your attention. You wait until Monday afternoon, then send a nice note explaining that you’re delighted to be so busy with work related activities, answer whatever you can professionally, and apply the appropriate script when he crosses a line. He comes back with a bunch more ways to get your attention. Now you wait until Thursday afternoon before repeating whatever appropriate script and appropriate thing there is to say.

    Honestly, there’s a lot to be said for a schedule even when a friend isn’t crossing boundaries. My friends know that I answer email and return phone calls on weekend mornings. (I don’t text, but if I did, weekend mornings.) I’m pretty much unavailable during the day. I might read their email if it comes in during the day, but nothing’s going to get answered until the following weekend morning.

  37. I think there is something very insidious and alluring that older men of this type count on, when they target younger women (certainly that was my experience when I was younger). It’s the framing of the woman being unusually mature, being understanding, being special. It’s particularly effective for those of us who struggled socially or who felt different from our peers. It’s a giant validation and it’s unfortunately pretty damn effective.

    I wish I’d had this column when I was younger, and I also wish I could give it to every single young woman — and I’ve also seen this dynamic among gay men — who may encounter this.

    Thank you, Captain Awkward. I’m also a woman in my forties and I work with university students, and like you I can’t imagine leaning on them for emotional support in the way LW has described Peter as doing. Many of these students are wonderful and amazing people, and they’re also still finding their way. Age and experience introduce a significant power imbalance. This type of behaviour is exploitative, even if there isn’t a sexual element to it (which there almost invariably is).

    LW, you’re doing everything right by setting boundaries! Bravo for your strength and awareness of how skeevy this is. Peter needs to prove he deserves you as a friendly work colleague.

  38. In addition to looking at the potential pervyness of the guy, I would encourage LW to look at this from her career perspective. This is a work-guy right? LW has a responsibility to her employer. So if any part of the BS from this guy is interfering with her ability to get her job done that’s a problem too. LW are you finding yourself putting off tasks to avoid this guy? do you need Pervy Guy’s input or approval to move your work on? are your relationships with other coworkers being affected? are you stressed at work beyond the normal level of stress for your position? are you changing your break/lunch habits because of him? are you worried that your potential for a promotion/transfer/raise/job recommendation are threatened by this guy? Hell, even if all the late night texts/calls are ruining your sleep and your too tired to function at work – that’s not cool.

    If you’re answering yes to many of these questions, please consider speaking to your manager, to HR, or to your employee assistance officer if you have one. You NEED your job and it’s not cool if stuff with this guy is putting your source of income and your career plans in jeopardy. If I was your manager, I’d want to know about this. Especially if he’s in any way able to influence your ability to get your work done and be successful on the job.

  39. I’ve come to find that I *loathe* the ‘wow, I’m being pretty weird, right? you’re probably uncomfortable with this, right?’ self-negging bullshit more than almost anything else.

    I’m a grown fucking woman and I don’t *need* your acknowledgement or permission to tell you when you’re crossing a line. If the behavior wasn’t bothering me in the first place, rest assured that it is NOW; if it was low-key bothering me, hearing that you know full well what you’re doing, and rather than making an effort to stop you’re passive-aggressiving me to accept said behavior AND perform the Reassurance Dance? Gahhhhh.

  40. 1. Establish a curfew. Straight-up, “please don’t text me after 10:00pm.” Don’t answer anything he posts after that time until the next day (learn to put your phone on mute after a certain hour), and then answer with “I asked you not to text me after 10:00pm. We can’t be friends if you don’t respect me enough to honor my basic requests.” Don’t let him weasel out of it – this shit ain’t normal.

    2. As a general rule, be very wary of older people that expect a lot of emotional effort from young people straight off. You’ve been adulting for 1-5 years. He’s been doing it for 20+. Why are you the one that cleans up all his emotional mess? Because the thing he learned in 20+ adulting years was to find newbies and take advantage of them.

    3. If he doesn’t cut it out, go to your boss. Tell him/her “he won’t stop with all these texts and i’m not sure what to do about it” and let the boss take care of it. You two are employees, you’re obligated to behave professionally around each other.

    1. Straight-up, “please don’t text me after 10:00pm.” Don’t answer anything he posts after that time until the next day (learn to put your phone on mute after a certain hour), and then answer with “I asked you not to text me after 10:00pm. We can’t be friends if you don’t respect me enough to honor my basic requests.”

      YES!!! Do this via e-mail, and give it to HR — it’s an obvious violation of a clearly-stated boundary.

      Include a screenshot of the text that shows the time, or add this sentence to your response, after “10:00m”:

      “Last night, you texted me at ___ o’clock.”

      Good luck, this guy is skeezy.

  41. LW, this is so wildly inappropriate of Peter. As an Old, I’ve sent an after-midnight email to my work colleagues exactly once: “There is water from the upstairs unit flooding our apartment. Pretty sure I won’t be in tomorrow.”

    I want to echo everyone here who is suggesting that you block Peter from your phone and social media. One of the benefits of being an Old is realizing how little other people’s Sads at your boundaries actually matter. Be abrupt. Be dismissive. Be borderline rude. Right now, Peter is causing you distress and unhappiness with his behavior. Take that distress and unhappiness and return it directly to Peter. It’s not your job to clean up his emotional mess.

  42. Sometimes I will commiserate, but then he will turn on me and ask these loaded passive aggressive questions like “you really ok with this?” or “am I being obtuse”, so I have stopped responding as I don’t have the time or emotional energy to deal with him right now.

    Some people are genuinely socially awkward and some people pretend to be socially awkward, counting on the fact that the discomfort they create in the people around them will ultimately get them what they want. However, it turns out it doesn’t actually matter which category a given awkward person falls into—whether someone’s awkwardness is intrinsic or cultivated, I’ve found that it’s best to state your problem with them directly, even if it makes you uncomfortable. Genuinely awkward people tend to be grateful for the feedback (and are often quick to apologize and to try to change whatever was offensive about their behavior) while people who were hoping to get away with something tend to realize that their normal tricks aren’t going to work with you and they’ll either have to escalate their unacceptable behavior beyond their own comfort zone (and to a point where their unacceptable behavior will become apparent to all) or they back off entirely.

    1. Good point.

      I’m reminded of a rollerskating unit we had in PE when I was in high school. One of the boys liked to flail around, pretending he was out of control while crossing right in front of people (likely only girls). One day I got tired of it and didn’t swerve to get out of his way. After we hit the wall together, he gave me this incredulous look, like, What the hell is wrong with you? (But he never did it to me again.)

      I predict a longer version of this response from Peter when he self-negs and you don’t swerve to get out of his way. Totally worth it.

    2. Yup. My story is a different situation, but it has the same sort of no-you-can’t-get-away-with-that result.

      When he was around the age of five, my little cousin went through a phase where he would suddenly shout “that’s it!”, lower his head, and charge headfirst like a bull into the gut of the closest person to him. My other relatives would gently chide him, but he kept doing it over and over again. The prevailing thought among my family members was “oh well, he’s just a kid, he doesn’t know what he’s doing.” So, unchecked, he thought it was funny and attention-getting, so he kept doing it. Eventually, he tried it on me and, instead of putting my hands up and trying to minimize the damage of a little boy barreling headfirst into my stomach, I moved out of the way. He caught himself before he ran into the wall and rounded on me, incredulous.

      “You moved!”

      “Well yeah. I don’t want you to run into me anymore. It’s not cool. And I’ll move every time you try to do it from now on.”

      Little darling stopped doing it entirely, at least to me.

      1. My mom actually pinched a kid from our church who had started pinching everybody because their reactions were funny, and it made him feel powerful. She warned him once, then pinched the shit out of him the next time he did it.

        He stopped. With everybody. (She decided that part of it was he didn’t realize exactly how much it hurt. Once he knew, he didn’t do it anymore.)

  43. OMG. LW, I don’t have any information to add that the Captain hasn’t already covered, I’m just here to provide even more reassurance that oh my fuck what this guy is doing is NOT OKAY.

    For starters, even if dude had no sexual interest in you (which he definitely does, this is 100% grooming behaviour), it would still be wildly inappropriate to message you late at night. It would be super fucking weird if he messaged you at 11pm, let alone 2am! My own friends would never message me in the middle of the night unless their home had just burned down and they needed to sleep on my couch. Now that’s me and obviously you get to decide how late it’s okay to send you messages, but since you didn’t specifically invite this guy to message you in the middle of the night, it’s super fucking inappropriate.

    And trying to recruit your friend?! NOPE. No reasonable human being who just has a job to do is going to waste their time pursuing someone they’ve been told repeatedly isn’t interested. That is creepy as fuck.

    Also you do not sound cold at all, LW. It is 1000% NOT YOUR BUSINESS that a much older work colleague is having legal issues and relationship drama. Even if you were a lawyer/counselor hybrid superhero, it would still be completely inappropriate for you to be his counselor or lawyer because you already work together. It is absolutely not mean to have boundaries. Dude should in fact have friends his own age to commiserate with. Even if he doesn’t (which would not surprise me at all since he has no respect for other people’s boundaries), it’s still not your job to fix it.

    If you’re comfortable not telling the truth, the whole truth, and nothing but the tru th so help you god, you could quietly change your facebook settings to not show him that you’re online or show him any of your posts, and tell him you’re trying to cut back on social media if he bothers you about it in person. You should also not feel any guilt about never responding to non-work messages or any messages that arrive at unreasonable (to be defined solely by you) times of day. LW, absolutely none of this ridiculous bullshit is your fault and you are not “mean” or “cold” in the slightest if you don’t like it when some creepy motherfucker shits all over your boundaries.

  44. If best to be able to be truthful politely 1-1. Some people need to hear it as it is- direct. If he doesn’t try to hear you out, then he is probably trying to be manipulative. I think it’s always good to try to consider direct honesty first.

    1. Definitely be direct, but NOT in person, especially alone with this guy. He is 100% interested in the LW and trying to groom her. She can tell him in a direct DOCUMENTED way that she’s not interested. No one owes an explanation to a creeper in a polite or potentially dangerous 1-1 way.

      1. This.

        LW, if you’re reading all the way down here, please do the following:

        * Establish a firm boundary IN WRITING — this is best done on your workplace email, not your personal phone — that he is not to call you at home after office hours and especially not after 8pm.
        * BCC that email to an address that is not in your work email that he doesn’t have access to. If he tries to retaliate, you have documentation he can’t reach.
        * As a response to the thread of 2am text messages, reply on your phone that it’s not OK to text you at 2am, ever
        * Screenshot all the 2am text messages, including the one where you tell him to leave you alone. Print that and keep it somewhere safe.
        * Print, sign, and date the email telling him to leave you alone after business hours and keep it somewhere safe.

        (Like, seriously, I work at a job where I’m on an on-call rotation and even then I don’t talk to Boss or Coworkers unless they call the on-call phone for an incoming project!)

        After that:

        * Block this man on social media, and lock your pages down, hard. (“I don’t allow coworkers on my social media” is a good general excuse.)
        * Put your phone in airplane mode at night.
        * Do not be alone with him in any place outside the places in your workplace environment where it is normal for you to be.
        * Do not ever get into his car with him. Take an Uber or call a friend. The only reasonable exception is that you or he are bleeding profusely and you’re on your way to the ER.

        Basically, don’t give him the opportunity to push your boundaries or groom you any further. If he doesn’t have any opportunities, he can’t take them.

  45. Creepy dudes: You know where a great place to go is if you want the attention of much younger women? The strip club! There are many ladies out there who will gladly morph into a nubile wife-mommy who is happy to put up with your bullshit **for a fee**. Leave your young female coworkers alone. Leave all your coworkers alone. Messaging coworkers at 2am is not an appropriate way to deal with your emotional problems. Knock it off. If you want Sexy Emotional Support, build a bridge to get over yourself, and then go pay for it like a decent person.

    LW, everyone else has already said it, but to reiterate: yes, this guy a creep; yes, your instincts are correct; yes, you should ignore his messages; yes, you should get HR involved. Good luck.

    1. Bad news: these guys are also creeps to strippers, and deeply resentful that they are being charged for emotional labor. These are the assholes who are sullen and grabby and don’t exactly treat the waitstaff well either.

      1. I’m a stripper too.

        Some guys are probably a lost cause of self-entitlement and some are just predators, but I would like “go see a sex worker” (of any kind) to be more common advice for straight guys barking up the wrong tree. Yes, it involves a guy having to admit to himself on some level that he’s not freely entitled to a woman’s time/body/sympathy/attention, and a lot of guys can’t handle that. Some can though, and there’s nothing wrong with wanting sex, touch, and/or sympathy. It would be healthier if they could get over themselves enough to just pay for it and get their needs met instead of slowly marinating in bitterness and entitlement until they become distorted and hateful.

        1. “Some can though, and there’s nothing wrong with wanting sex, touch, and/or sympathy. It would be healthier if they could get over themselves enough to just pay for it and get their needs met instead of slowly marinating in bitterness and entitlement until they become distorted and hateful.” +10000 to all of this.

  46. The bad news is that there is no magical age at which that shit from older guys stops. At the age of 50 I signed up to a social networking group targeted at over 40’s, specifically as a way to socialise that wasn’t dating, and at my first (and last) event got creeped on by two guys who must have been at least 15-20 years older than I was. One was particularly bad: although he didn’t actually touch me he sat next to me at the table and leaned into my personal space (stopping just short of putting his arm on the back of my chair) and started bemoaning his unsatisfactory sex life with his current partner – in front of a dozen other people and while we’re all trying to eat. No-one else seemed to even blink at this behaviour. I was too stunned to act assertively and tell him to knock it off, although I did manage to turn down the request by older guy #2 for my phone number. Then I ran far far away and never spoke to anyone in that group ever again. My experience is that relationship confidences like this are at best a prelude to being hit on for sex and at worst a testing of boundaries before progressing to sexual assault, and you need to shut that conversation down ASAP and use whatever resources you have available to help you do that.

    1. This. I went to a Meetup in the town where I live. First time I went, it was with a male relative. I went a couple of times after that…once was okay, but the second time I realized that there were almost no women in the group because the men in the group would try to pick them up AND pass them around like shared sex toys. They were more subtle than some, but it was still dead obvious when there were enough pints of beer involved.

      The few women who were there were very up front about warning other women in the group about what the lay of the land was.

  47. One quick note in case he does try the passive-aggressive “I’m so pathetic, how can you stand me” answer: I think the best answer to that crap is a very matter-of-fact ‘I hope you get some help with those feelings, but I’m not the person to give it to you’. Followed by an immediate end to the conversation (hang up, close chat message window, walk away if you’re talking in person, etc.) Wish I’d had that one years ago.

  48. I want to test a hypothesis: How likely, does anyone think, would this situation be even -considered- not creepy and wierd, if the 2 AM caller and not-really-a-friend feelings dumper was a female, or female presenting?

    I suspect all potential sympathy and second-guessing (on a reciever’s part) would go straight down the drain. Ladies are supposed to handle their “hysterical shit” (as I once overheard from an ER doctor) themselves.

    After a few years of hearing so many of these emotional labor stories, I’m starting to wonder how much of my instinct to ‘not bother’ anyone, even in an emergency, or of ‘overreacting’, is acting internalized misogny.

    1. TBH this is why I don’t have any patience for men who indulge in this behavior. I am not talking about someone who’s confiding in multiple friends, or saying “I’m having a tough time, could we just hang out over breakfast at X place and talk about comic books for a while?” I am talking about boundary pushing bullshit like what this douche is doing to the LW. And when dudes tried this on me I got angry, because fuck this. I am sorry you are having a hard time Mr. “I’d like to pay you for your expertise but first I want to dump my complaints about my wife on your lap.” Mr. “I know I’m your boss/your orgs board member but I’d like to use you as a sounding board because you’re a lady shaped being and that’s what your for.” I am expected to suck it up. I am expected to take no for an answer or read between the lines, and move on (“he’s just not that into you”, etc.). I am expected to not cling to people.I am expected to be appropriate. I am expected to Handle My Shit–even when I was in the throes of clinical depression, FFS. It never occurred to me to dump this on anyone’s lap, let alone a sexy dude I worked with or knew through friends.

      So if *I’m* expected to handle my shit–even when my brain weasels go on a bender–I goddamn well expect men to handle theirs, and I get pretty shitty with anyone who tells me how cold I am for my attitude (yes, I’ve heard it and I’m not here for that crap).

    2. >>I want to test a hypothesis: How likely, does anyone think, would this situation be even -considered- not creepy and wierd, if the 2 AM caller and not-really-a-friend feelings dumper was a female, or female presenting?

      I suspect all potential sympathy and second-guessing (on a reciever’s part) would go straight down the drain. Ladies are supposed to handle their “hysterical shit” (as I once overheard from an ER doctor) themselves.>>

      Mmm, it depends. In this situation, yes, absolutely. But I am also reminded of a straight male friend of mine who collects Emotionally Complicated Ladyfriends like a shelf of tragic Hummel figurines. And I note that Emotionally Complicated Guyfriends are MUCH more rare in that landscape. And so it is still also an eroticization of the suffering / support dynamic.

      Note I don’t think it’s bad or wrong to have problems or be kind of dramatic/Tragic, in and of itself. It’s the pattern that worries me. I can just about guarantee that LW is not the first young female coworker this dude has bothered.

  49. LW, the two of you are not getting your wires crossed. This dude is purposely crossing both clearly-stated and socially-acceptable boundaries because he places what he wants above what anyone else wants. He made that very clear: “I do what I want (regardless of the fact that I was told no and that the girl has said multiple times that she is not interested).” That is not ok. And you emphatically Do Not sound cold. You sound like somebody who is exhausted from having to constantly be on guard and defend themselves, and is getting worn down by it. So I’m going to tell you what I wish someone had told me when I was younger:

    A guy who will not respect your no over small things, will not accept your no when it comes to the really important ones either. This is boundary-testing behavior. It leads nowhere good. To reiterate what the captain said, PLEASE keep your guard up around people like this. Freeze them the hell out. They are not owed a warm reception.

    See also: “No” is a complete sentence and a titanium wall. Make it so. Run like hell from anyone who disagrees.

    I think you have a perfect script within your own letter: I don’t have the time or emotional energy to deal with [this]. Period. You can insert “professional knowledge,” “training as a therapist/counselor,” “billable hours available,” “money in my account to cover,” “hours in the day,” “room on my calendar,” “interest in the level of involvement you need/want,” “sympathy reserves,” “overall give-a-sh!t” etc, in place of “time or emotional energy” and any one of them would be perfectly fine too. You don’t want this. That is all the reason you should ever need. Nobody should be trying to order services from you that are clearly Not On The Menu.

    If you can set your cell to only take calls from certain, important people during non-business hours and unplug your land-line when you go to bed, even better. Answer only the texts you want to, or none at all. But please do not feel obligated to respond to texts or take his calls just because he escalates if you don’t. You are not answerable to him just because he has decided this is the time he wants to talk, especially not in the off season, most especially not about his personal issues. You do not owe him conversations that test your limits, no matter how unfriendly you might feel for saying it. You do not owe him anything at all. It is ok to be forever “too busy to talk right now” when this guy calls. His escalation when he doesn’t get your immediate attention is very much a part of his refusal to take no for an answer. Not letting you sleep at 2 AM is too. He is trying to *force* you to do something that he is well aware you don’t want to. He is trying to wear you down enough to get past that (very reasonable) boundary. Reclassify this dude as, “thought he might be cool at one time, until he showed me who he really was” and spend your time and emotional energy anywhere but on him, in places and with people who know how to take no for an answer. Because even if he is just obtuse, can you really afford for him to be obtuse when you say, “I’m not interested in being your girlfriend/intimate partner/on-call person you use for sex/anything other than work-friend” and keep ignoring your no?

    1. “A guy who will not respect your no over small things, will not accept your no when it comes to the really important ones either.”

      So much this! I went on a few dates with a guy I knew through work. The deal breaker for me was when we were out for drinks and he asked me if I wanted fries. I said no twice, and he ordered them anyway. When he asked me why I wasn’t having ant, since he had ordered them for me, I said that I’d already told him I didn’t want them.

      My thought process: if he didn’t hear me say no over a plate of fries, what else won’t he hear my no about?

      1. You know that scene in the movie Hitch, where he meets The Girl for the first time, and they’re in the bar, and she’s had a rough week, and she’s all prepared for him to steamroll her with questions, after she’s made it clear she’s not interested (right now), and instead he says [paraphrased], “Nah, that’s ok. It’s nice to have met you, Sarah Melas. I hope you enjoy your evening,*walks away*” and you can almost hear the record scratch in her head by the look on her face, because literally NO ONE has EVER done that? Yeah, that scene? That was an almost play-by-play of how I met my husband. I declined an invitation to dance and he said, “Yeah, I figured. But you seem like an interesting person, so I wanted to say hi. I’ll be over here with my friends if you get bored later and want to chat,” and that was all. He turned around and casually walked away like it was the most normal thing ever. As if I had not just witnessed a legit miracle. As if he knew already that the sky most decidedly would not fall in if he did not get his wish for my attention granted immediately. Like he’d be alright with his life still. He didn’t try to ‘break the touch barrier’, or try to drag me out on the floor anyway, or start dancing/humping my leg right there, or whine like a lost puppy, or pout, or beg, or cajole, or open negotiations, or… nothing. Just walked away.

        For the first time in my life, my ‘no’ actually had power. ‘No’ meant something. And I was stunned by it. I had this surge of bright realization hit me – that we *should* be able to expect that out of men, all men, especially when it comes to how we spend our time and what we do with our own bodies – there’s no good reason at all for this to be so unusual! What I had been expecting was so backwards. It should have been a big deal every time my ‘no’ had been previously ignored, not the one time it was heard! So, I recalibrated my expectations then and there. And I did accept his invitation to chat later on. And for 15 years now, not once has my ‘no’ ever been ignored by that man. I run from people who attempt to bulldoze over a ‘no’. I wish I had done that much sooner. I wish I had even known that I could. But my ‘no’ had been so routinely ignored until then, it’s a wonder I even bothered saying it. That was my *normal*. And it shouldn’t be. We should not be gracing people with our presence who are not capable of handling a simple ‘no’. Not ever. You absolutely made the right call!

        1. A friend of mine once told me, “I knew I wanted to be friends with you the time you offered me a beer, and I said ‘no thank you, I don’t drink’ and you said ‘okay’ instead of ‘why not?’ or ‘are you sure?’ or anything else.” I’ve jokingly said that my response was because I mean “sweet, more beer for me!”, but really it was because I couldn’t imagine confronting someone I’d just met over whether or not he wanted a damn beer.

          1. I have spent so much of my life defending my decision not to drink. I too would consider you a special soul. Hell, I don’t know you and I D* consider you a special soul.

          2. Another vote here for your special soul status.
            It’s pretty startling how many people seem to take non-imbibing personally.

  50. All of the commentators and the advice are spot on. It took me years to learn how to do it, and even then I was fuzzy at best – but then I ran into a Unicorn. An older gentlemen capable of being friends with younger women from work without crossing boundaries or getting weird – even if the context got weird (Turned out we were both into the same kind of Risque Naked People Here Events). Since then I sometimes ask myself “Would K do this?” and the answer is always so clearly NO that I immediately know someone’s getting shifty.

    All you need to know is that you’re uncomfortable. That’s the bar. Trust yourself. 🙂

  51. Unsympathetic reading: He’s a predatory creep. That’s all.
    Sympathetic reading: He’s unhappy with his life and using you for therapy – with an added splash of titillation which he can justify to himself because it never goes anywhere. As many an unhappy person does before taking a hard look at things and getting themselves in order and-or getting proper therapy. Doing it to junior colleague takes it to a new level of audacity. Being around a much younger person may have triggered some reminders of his past (true of and worth bearing in mind in most age-gap situations, even fairly healthy ones) and those reminders could be painfully intermingling with the breakup. All his problem, not yours.
    Bottom line: He’s making you feel horrible and you do not have to accept it. Captain’s advice is spot on.

  52. Ugh i needed to read this today as I am in a similar situation (now an-ex situation as I spoke to HR and began dealing). LW you have all my sympathies. I believe in you, and I am sorry this happened.

  53. Spot-on advice! LW, I’m sorry you’re going through this, and sending you support and solidarity. I sincerely hope that he will respect your boundaries and respond well, and not threaten your job at this festival.

    As a former freelancer, I’m concerned that a festival set up might not have a clear cut HR department to go to. If it does get to a place where your job might be compromised and there isn’t HR, think about who would be a good outlet. Is there a production manager? Who hires or is in charge of Peter that you could speak to? Your job should not be on the line for setting reasonable boundaries, and it would be good to identify a plan for who to speak to if it comes to that.

    Best of luck!

  54. Great post. My Peter was named Chris, and he would hang in my doorway at work and talk about things I mostly didn’t want to hear about. At the time, even though I was miserable, I was pretty sure that some of this was my fault. I escaped to another job, and the following year, found it immensely satisfying to learn that he had been arrested for prostitution.

  55. LW, I wrote in about a similar situation a while ago. I was several years older than you, but all that means is that you may run into this again in the future. The older guy did the same thing – took our casual work relationship and started to complain about his love life. I was trying to be nice and listen because that is who I am, but I think these guys look for that in the women they target. This jerk lured me to his office under false pretenses to hit on me then denied that was what he was trying to do. I left as soon as possible and have avoided him ever since.

    You’ve done the right thing by limiting your responses and I agree completely with the Captain’s advice. It is a sucky situation. Good luck! And remember, it’s not your fault.

  56. The Captain wrote: “When creeps and bullies are told to stop doing something, they use “negs” or “typecasting” as manipulation tools. They say stuff like “Whoa, I didn’t realize you were so uptight,” “I thought you were mature and you could handle it” or “I thought age doesn’t matter in friendship like ours” or “You’re right, I’m so pathetic, how can you even stand me?” (stealth version, trying for pity) or “But I asked if it was okay and you didn’t say anything, so it’s not fair that you would ask me to stop now” to try to get you to defend yourself or comfort them by doing what they want you to do/what you don’t want to do. The fact that you don’t like this and don’t want it to continue cancels out any argument he might make.

    One way to defuse typecasting tactics like this is to agree with the neg instead of arguing with it, for instance:”

    And then she offered a list of scripts to respond.

    Sometimes, a longer script is harder to think of, and it might just imply the convo can continue.
    So i want to suggest another tactic for your arsenal.


    Note that it’s a sentence. A statement. It’s not a back-and-forth.

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