#848: Suggestive Comment Guy Strikes Another Friend Group!

Hello Captain!

Last summer, I worked at a really amazing job and met a lot of people who I really like spending time with. I am fortunate to have developed a solid friend group and gained a long term job at a related company for the first time (my field is competitive, and difficult to find employment in), but there’s one guy, Derek, who’s making me uncomfortable.

Derek and I worked on the same team, and became very close – we have common interests/hobbies and had compatible work/social styles. He’s aware that I’m in a monogamous relationship, and was completely respectful towards me both at work and otherwise. After we left our summer jobs, we continued hanging out and texting a lot, and I considered him a good friend.

Recently, though, he’s made some really creepy and borderline sexual comments over text and in real life. I’m trying to slow fade our friendship, but things are complicated by my inability to completely avoid him – I don’t text him or make plans anymore, but he’s my new manager’s roommate now, and comes to our social gatherings. My new coworkers are starting to notice something is up, but I’m a shy person and I get really uncomfortable talking about this sort of thing, so a few of them have commented that we have “something going on”.

What’s a good script for heading this topic off when confronted by gossipy coworkers? I have a solid Team Me, and my boyfriend’s aware of the issue, but I don’t know how to explain that this dude is being unwelcome and WEIRD to people I’m not that close to. 😦


Not your personal Lana del Rey, Derek.

Dear Not Lana Del Rey,

A suggested script…for Derek…is to text him and say: “Hey, your sexual comments lately are weirding me out. Please stop.” Remove his Plausible Deniability Shield and address the poor behavior directly. It will feel nerve-wracking and then amazing. See also: “Wow. Inappropriate.” “I don’t like talking about that.” “Hey, you are probably joking but I don’t like that.” “Creepy! Stop now.” 

If he says “Those were jokes” then you can say, “Well, I didn’t find them funny and I want it to stop, so there should be no problem!” Save & document the texts he sent you and the comments he makes, btw, because if you still work at the same company this is or can soon become a human resources issue. The first question anyone in HR is going to have is the first question your mutual friends are going to have, i.e., Did you tell him to knock it off?

I know women are socialized not to be so direct, but I promise, you can do it! It can be hard to speak up when it’s not a habit for you, but it’s also between hard and impossible to get an entire social group to help you fade out on a dude for you if you haven’t articulated what’s going on. If Derek were a one-off friend with no connections to your day-to-day life, you fading out on him would be enough to get him out of your life, but since he’s always around, being direct with Derek is the quickest path to the change you want to happen. You can’t count on hints and indirect pressure to send Derek a message. Hints don’t work. Hints just let clueless people keep swimming  in the Sea of Not Getting It and creepy people splash about in the Lake of Plausible Deniability.

If Derek apologizes and immediately cools it with the comments, you won’t have to worry about him so much at parties. It will feel weird for a while but then he’ll either be too embarrassed to be around you or he’ll behave himself and it will go back to normal. If he doesn’t behave himself, when the feeling that “something going on” is in the air with your coworkers, you can say, “We were good friends, but he made some sexual comments to me and I’m keeping my distance for now.” That has the advantage of being the truth. If he escalates his creepy behaviors at work functions, talk to human resources and show your documentation. If you end up having a heart-to-heart with your manager/his roommate, keep in mind that people who are inexperienced at being bosses often want to help but don’t know how. Suggesting something specific that they can *do* is a way to help get what you want. “I’d like a heads-up if Derek is attending events, so I can decide if I want to be there, and if he publicly makes creepy comments to me or others, I’d like you to say something to him about it and not to have it always be on me to deal with it.

Finally, it’s cool and fun to hang out with people from work and make great friendships there! I enjoy doing that a lot! But take it from a middle-aged lady: Cultivate friendships outside of work and outside of that one  friend group. You need some social streams that don’t cross with your livelihood and where Dereks do not presume to tread.

You’ve got this and it’s gonna be ok.


Captain Awkward






89 thoughts on “#848: Suggestive Comment Guy Strikes Another Friend Group!

  1. A+ to this advice…especially the short responses to texts. Creepy, not cool is a complete thought.

    I like the idea that we don’t have to engage in a lot of painful discussion to establish a boundary. A simple nope and subject almost always works just fine.

    Double A++ to not having your eggs in one social basket. Way too much pressure on any one group to BE THE ONLY THING.

  2. Solid advice from the captain, hopefully being direct will be enough for him to ease off and if not, you’ve gpt something very explicit and documented as well as adding a kick-ass feather of bravery to your cap. You can do it!
    Also seconding the varied social groups. “Dont shit where you eat” is a way too strong a phrase and for those of us who love hanging out with cool coworkers….bit it has some truth since if things go south it can have a knock on effect or priorities can be a little weird. Cultivate more social groups and you dont have to worry and meet cool people to boot 😉
    Good luck LW!

  3. Seconding the directness point so hard right now. I am a person who cannot understand hints, and I’m also really bad at giving them and used to be terrified about being assertive and appearing bossy. When you finally get over that hump, especially at work, it’s so satisfying. I’ve had to do it a lot as an Orientation Leader and at my work, where I deal with a lot of younger people who haven’t exactly graduated from Anti-Oppression 101. “Hey, knock it off” and “Pick a different word… no, I don’t care that you don’t believe that word is bad, pick a different word” have become broken record phrases. A word of advice, habits are powerful. If you pick one phrase that you are always going to use when Derek’s being weird/creepy, and then repeat it a lot both to yourself as practise and then to him, it will become second nature and be a whole lot easier to address the behaviour, because it’ll be habit and not a scramble to find words.

    1. Yes, the practicing! So important. And be so so unambiguous. “You’re being creepy again, stop it.” If he does it in front of people, always preface comments with something that makes it clear this is not the first time, and end with a demand that he stop. “As I’ve told you, that is a creepy thing to say. Stop it.” “I’ve repeatedly asked you to stop saying gross things to me. Stop it.” “I don’t care that you don’t think it’s gross, I think it’s gross, so stop it.”

      It is appalling that Derek is doing this to you, and I hope that he stops immediately and this does not escalate.

  4. Also, serious side-eye to this guy rooming with your manager and the potential risk that can entail for you. That has a lot of potential to get ugly if this guy is a real asshole. Your manager, living with him, is likely to be on his side and give him all the benefit of the doubt, plus the direct access to information about you and your work. The potential for this guy to influence your manager’s perception of your work performance, shudder. So document, document, document and hope you never need to use it. Maintain professional front and enforce communication standards with manager.

  5. LW here – Thanks Captain!!

    I’ll try some of those scripts out, I definitely have a super hard time being direct 😩 It seems a lot easier when I’m making work related decisions, but I get really anxious about it in my personal life.

    To clarify – we’re no longer working at the same company, but we’re employed at related companies that both attend the same programs and have the same funding sources. So luckily, I don’t have to see him daily, but when we have mentoring events etc I still do. Your instinct was correct, also -my manager *is* extremely young, I think he’d be willing to help (and has taken positive action in similar situations) but I’ve been unsure of how to bring it up til now since we don’t really have a lot of precedence for it.

    I’m usually conscious about varying my hangout time with friend groups, but lately I’ve been working so much (agh, startups) that I’ve fallen into the trap of hanging out with only work people. This might be a good kick in the proverbial butt to make plans with friends I haven’t seen much of lately.

    Thanks so much again, this helps a lot!

    1. I’ve had good results from asking a friend or colleague to stay near me when X is nearby as he makes uncomfortable remarks when he gets me alone. It’s both non-confrontational and a bit of a nuclear option.

    2. LW, it might help to phrase this whole thing around work for you when you are psyching yourself up to set your boundaries. Like, “I need to do this now before/because it affects my work.”

      I’ve been accused of being “too nice,” but once my work is threatened, I stand up for myself much more than I would if it was just personal.

      Good luck!!!

      1. rhythla said: I’ve been accused of being “too nice,” but once my work is threatened, I stand up for myself much more than I would if it was just personal.

        Yeah, women are socialized not to stand up for themselves.

        * In personal life, some abused women run not because they deserve better, but because sibling/child does not deserve the abuse.

        * On the subway, women will stand up for someone else being hassled though they just cringe when they themselves are hassled.

        * At work – save the work, if not the self.

        Sometimes, its just best to visualize Best Friend being hassled by Smarmy McSmarmypants. What would you do then?

        1. Be your own best friend!!! So, so important to take a step back sometimes and it really helped me break out of being socialized to never put myself first because I’m just lowly woman, not worthy as teh menz and teh kiddz.

    3. One thing that really helped me become more direct was reframing it in my own mind as “giving him the benefit of the doubt.” Like, the generous interpretation is that he does not want to upset you, so if you’re like, “Hey, not appropriate!” and he’s a good dude, he’ll say “oh crap, I’m so sorry, I’ll knock it off.” Right? Like, I have Inappropriate Comments Friends where suggestive jokes and faux flirting and so on are part of our banter, and Definitely Not Inappropriate Comments Friends where that is very much not the case (this category is by far the larger one; it takes a certain kind of relationship to be an Inappropriate Comments Friend), and if I had thought that someone was an Inappropriate Comments Friend and they weren’t I’d want them to say something, because I don’t actually want to be creepy or make anyone uncomfortable.

      And of course, you can also think of it as a fact-finding venture, because if he replies with “well EXCUUUUSE ME, princess” or “can’t you take a joke?” or by persisting, then you now know something very important about the guy.

      Now, obviously, you are under no obligation to give a guy who is making creepy comments the benefit of the doubt. At all. But for me, framing it that way made it 100% more likely that I’d speak up, and so it might be useful to you.

      1. The ideal answer to “can’t you take a joke” quite often is a plain “Nope.” Or “I only like jokes when they are actually funny.”
        Jerks like that seem to think that you will back down instantly if you falling into the category of being a ‘good sport’ is being threatened. If you happily accept being categorized as a grump, they often run out of places to go with their bullying.

        I call remarks like that ‘off-switches’ or ‘trump cards’, because they are supposed to be unanswerable, switch off your will to argue and make you give in instantly, much like calling a girl fat is supposed to turn her into a quivering mass of insecurity that would never tell a guy his pick-up lines/freshness of breath/sartorial choices etc. leave a lot to be desired.

        I’ve also often said “I’m German, I’m not supposed to have sense of humour”, but obviously that does not work for everyone :-p.

        1. Hah! Yes. I have looked someone dead in the eye and said, “Yes, actually, I am one of those humorless feminists.” He started to laugh nervously while I stood there quite calmly, not laughing, and didn’t bother me again.

          CS Lewis is a writer who has a lot of flaws, but I have always loved a bit from the Screwtape Letters where he says, essentially, that for many people being accused of not having a sense of humor is such a dire insult that they will agree to almost anything so long as it will deflect that accusation. There is a power in turning that script on its head.

          1. Yup. Agreeing to that kind of accusation is like verbal aikido – by giving in, the attack runs into emptiness.

          2. Or also, if you aren’t good at deadpan, you can laugh at the very idea that you can’t take a joke. I am *hilarious* so when someone accuses me of no sense of humor, I honestly laugh at them as I say “yeeeah, that’s me, noooo sense of humor.”

          3. This. I’ve found that when someone accuses you of being humorless/a bitch/a coward/whatever,
            if you say “yep, that’s me” and just look at them in expressionless silence, they’ll usually figure out that what you really mean is you don’t give a damn what they think you are and you’re not going to put up with their shit to prove otherwise.

            If the joke is really over the line, you can put it in as many words to call them on it: “I don’t take jokes about sexual assault.”

            You can also ask them to explain why the ‘joke’ is funny: if they actually take the bait and try to explain, they’re doomed.

            I *hate* “it’s only a joke.” It’s the first refuge of cowards.

          4. Yesssssss owning the “humorless” label is really so empowering. However you want to phrase it or whatever noun you want to stick on the end of it (“humorless feminist,” “humorless b****,” and I think I’ve used “humorless sod” before), people never know how to react and it is amazing.

          5. Mine is generally, “I have a GREAT sense of humor, it’s not my fault that wasn’t funny.”

          6. Also, if he says anything to try to imply that you’re a prude for not having the flirty/interested reaction he wants you to have when he makes sexual comments at you, a similar strategy may be very effective. As a teenager I once had a really persistently creepy coworker who would not stop with the sexual harassment, and our HR was shite so I was on my own. Finally one day he said something about how uptight I seemed and I just looked him square in the eye and said “Yes, I am extremely uptight. I am a celibate lesbian and a devout Catholic and an utter prude. And you need to stop harassing me. Get it through your head.” It worked like a charm.

          7. Just echoing all the other responses to this since nesting is maxed.

            Embracing the Humorless Bitch is empowering as hell. It makes their attempts at…whatever… visibly miss and shields you from any attempt at insulting/negging you into compliance. Guys pull that nonsense because they know we’re conditioned to defend our sense of humor. Don’t bite.

        2. Another response could be the earnest cluelessness thing – “oh, that was a joke? (puzzled face) Nah, jokes are funny. That wasn’t.” But my favourite CA response is “wow.” Raise eyebrows past hairline, turn away. Variation: “really?” with disbelieving just-smelled-poop expression… aaand turn away.

          But hey, LW – however you choose to stomp his crap down – I wish you luck. It’s horrible feeling uncomfortable.

          1. Ha just saw anisoptera said same kinda thing below. But yeah. Paraphrasing Captain Awkward’s advice from other posts, don’t try to smooth the moment. Just let it *be* awkward. If anyone’s going to stumble over the silence or laugh uncomfortably, let it be Derek.

          2. > But my favourite CA response is “wow.”

            I do believe that the good Captain got that one from another wonderful advice columnist named Caroline Hax (who may have gotten it from a reader). She is so good. She’s like the mainstream press version of CA, with all the brains and snark and none of the swear words.

          3. Oh weird – I meant my comment to be up here, not way down there on an unrelated thread. I guess I was more distracted than I thought when I wrote it.

        3. If you’re looking for a less-nuclear option than a deadpan “I have no sense of humor”, you can try these:

          Them: “Jeez, it was just a joke!”
          You: “Oh, well… I’m sure you’ll get the hang of it soon.” -project sincere compassion, like you’re consoling a friend on an embarrassing failure-

          This has the added bonus that if they get offended, you can turn around and use ‘can’t you take a joke??’

        4. Yes, I love the agree-and-confuse tactic. I use “apparently” or “apparently not” as appropriate. (Most recently, at a pub, “Oh, you’re one of *those* women.” “Apparently.”). It works with many delivery styles: deadpan, light and oblivious, and — my favorite — super-ultra extra-wicking patented technology dryness.

    4. You sound pretty cool, so I hope it goes well for you. 🙂

      And yeah, I think there’s another reason to make sure work authorities are aware. Your sign-off suggests he’s calling you his ‘personal Lana de Rey’ (ugh), and if he is … then he’s wrapped up in several layers of fantasy. He’s got a fantasy based on Lana del Rey and he’s looking for someone to put it on, and he’s got another fantasy that you don’t mind if it’s you. He needs a dose of reality.

      Especially because – you notice how he was perfectly appropriate when you were working together, and his creepy comments started when you were no longer employed by the same people. Ie, when his chances of getting fired for harassing a co-worker changed? He may be fantasising, but he’s not that naive: he knows where he can’t get away with this crap. So bring in work-related people: it’s a deterrent that’s been proved to work in the past.

      1. I know squat about Lana Del Ray other than that she did a song for Maleficent and I’m still creeped out.

    5. As far as bringing it up with the manager, maybe something like this: Manager, Derek has taken to sexual innuendo with me. I’m uncomfortable with it, and I’d like you to back me up. I’m telling him to cut out the sexual comments around me, and calling him out if he continues. It would be great if you’d do the same.

    6. Just a quick tip that’s helped me be more direct via text, at least: after you send the “Not cool” text, shut your phone off or put it away where you can’t look at it (or power down your computer, if you email) and then go do something else, immediately. It saves you from sitting in horrible suspense waiting for the Undefined But Definitely Life-Ruining Response that you fear, and gives you some time to calm down and recenter before you come back to the situation.

      It’s very helpful to be strategic about this, and make a plan to send the message right before you have to do something very mind-consuming for a couple of hours – especially if that something requires you to be disconnected from personal devices/communication at the time.

  6. As an HR manager, I just want to reiterate that this can be an HR issue even if the comments are being made outside of work. If it continues after you tell him to cut it out, bring it to HR.

    1. It’s not clear to me whether the writer and Derek are still co-workers. If so, and if the writer’s boss is also Derek’s boss, that’s even worse. Managers usually shouldn’t socialize with or, worse, be roommates with their subordinates because of these very issues.

      1. I think that if the manager is bringing someone to work functions who has a history of harassing staff, it is Very Much an HR Issue. The manager is responsible for creating a non-hostile work environment, and bringing Derek around is an issue.

        (A simple thought exercise may help: If I’m a manager, and my spouse begins to harass my staff every time I bring them around, that’s on me the moment I’m aware of it. I don’t see any difference if it’s my housemate, parent, or anyone else — if I bring them, and I know they make my staff uncomfortable through inappropriate behavior, it’s on me as the person who a) invited them and b) has direct responsibility for creating a non-hostile work environment for my staff. I also don’t consider a social event an exception; if it’s a work social, it’s a work social.)

      2. The manager-as-Derek’s-roommate issue is messy, but it doesn’t excuse the manager from actually managing their employees. It could potentially be an issue for LW depending on the type of person the manager is and how the company handles allegations of harassment. I would hope that HR and the manager will understand why it’s being brought up and act professionally, but I know that life doesn’t always work that way in reality.

    2. A friend of mine had this prob – creepy-work-guy deciding not to hear “Stop speaking and go away” no matter how it was said.

      Finally one day, when he came up to her desk to casually lean there and start some new crap she held up one finger, gave a cheery “Ooh, hang on a sec, hang on,” opened up an email to HR and then went “Right, sorry, go on!”.

      And then she let him go on as she stared him dead in the eye while touch-typing into the email every single thing he was saying, typing when he spoke, pausing when he paused etc. When he realised what was happening and said “Er, what are you doing?” she smiled and answered breezily “Just emailing this word-for-word to HR.”

      Apparently he went quiet, went white and walked away. And never approached her again.

  7. Terrific advice to call him on the behavior and tell him to knock it off because you don’t like it + documenting it calmly + deciding not to attend events where he is.

    He will get the message and hopefully will knock it off.

    But be prepared for if he escalates it for a little bit. If he does, then keep doing everything the Captain advised, especially documenting it carefully and calmly. Also if you do go to places he does maybe don’t drink?

    I had a Work Derek although we were not good friends before he started his creepy behavior. My office used to go out for Friday night drinks and people would drink and some would get tipsy and that was perfect for Derek’s plausible deniability of touching me/trying to kiss me/making sexual comments then saying “I must have been drunk lol sorry I don’t remember.”

    But he was not drunk when he made a sculpture of a boner in blu-tack (I don’t know what you call that in American sorry) and stuck that to the divider between our desks before leaning over and saying “I know you’re thinking about it.”

    He was not drunk when he made similar sexual comments to me during the work day.

    I complained to his manager who moved him to sit elsewhere but didn’t take it seriously and suggested I was “egging him on.”

    If you are a manager and someone makes such a complaint PLEASE TAKE IT SERIOUSLY.

    Derek sexually assaulted me at our Christmas party and it was horrific and no one took it seriously. A lot of people including me had drunk alcohol and I was a little drunk but I remember everything that happened including how I said NO very unambiguously. A while later I left that company. It was years ago now but it still makes me feel awful.

    These things can escalate.

    1. I’m so sorry that happened to you, and that your manager and company were unsupportive and unhelpful.

      And we use blu-tack in the US, but sometimes call it poster tack instead/as well.

    2. What the hell is it with harassers and boner sculptures?

      When I was in college, I briefly worked at a pizza place where one of the shift managers was both a harasser and a good buddy to the store manager. One of his favorite things was to sculpt boners out of leftover pizza dough and find an excuse to call one of the gals from the front back into the kitchen. And you couldn’t complain to the manager because that douchenozzle would start asking questions that reframed the situation as your fault. I quit as soon as I could find another job. That was over 20 years ago, and my face still gets hot when I think about it.

      1. I’m thinking about that for you, Courtney. I’m grabbing the dough, squeezing it, banging it against the counter and throwing it into the oven at 500F. Slamming the door shut and back out front with one finger on each harm waving buh-bye. Can you guess which finger??

  8. Captain, can I just say how much I’ve appreciated your cheerful comments about being middle-aged / your perspective now that you’re 42 / how awesome it is? It’s delightful. My mother’s also cheerfully announced how much she likes herself more now that she’s in her mid-50s, and that every decade was an improvement. You have a way of saying “Wow the world looks different from this angle” without invalidating the other angles, because you remember those, and you value and have compassion on those points of view too. So, thank you. Thank you very much.

    1. The only thing I want back from my 20s is my non-gray hair. And possibly my ability to function with less sleep.

      1. LW if you’ve read the archives here you’ve probably already encountered this advice, but can I just say that training yourself to just let things be suuuuper awkward and allow long, horrid silences to just hang there without you fixing them is like a magical power? It feels terrible at first. Every fibre of your being will cry out to smooth things over and laugh them off and maintain the social situation with minimum drama. But actually, if you can drop a short blunt statement and then just stand there and maintain eye contact in total silence it *really* strengthens your message. Hell, even a blank silence where you say nothing to a comment you don’t like is a powerful message that you don’t like it.

        If you’re anything like me this will be hard as hell to learn, because you’ll have been trained from birth to make sure everything is cool and everyone knows you like them and don’t blame them and are a super chill girl who of course is laughing at their joke. The first time I did this my hands shook. But it turns out it gets easier with practice. And then you can say things to weird comments like “not cool” with a brief grimace and then let the silence hang until they back out of it. Or if they say an variant of “I thought you could take a joke” you can get comfortable with a blunt “just stop doing it” or “nope” and then…more horrible awkward silence.

        Some people will respond to this with negging – like “you’re such a hardarse” in an attempt to get you to soften your demeanour to prove them wrong. Don’t do it. I find a deadpan “really?” with a raised eyebrow and the most Devil Wears Prada expression I can manage is a good response to this.

        There are some guys who will be determined to continue being horrible despite this (hell there are some guys who’ll continue being horrible despite police intervention) so record everything and be prepared to escalate if you have to, but it removes the shroud of plausible deniability and there are lots and lots of people who’ll back off.

        This is also, BTW, fantastic for increasing your authority at work, especially as you move into more senior roles where more confidence is expected. Never apologise, never explain isn’t great advice for all situations but it was made for this one. Don’t explain. Don’t start a long discussion. Don’t apologise for drawing the boundary.

        Remember – this guy is being rude and awkward – it’s his fault and you’re well within your rights to respond to him like he is.

        1. Oops. This comment was for a thread further up… Heh. Although, yes, I also don’t miss my 20s either. 🙂

  9. “Cultivate friendships outside of that group”

    This really struck home with me. There is someone I’m trying to do a slow fade on (to? from?), but we’re in the same social group and attend the same social events. Since I don’t want to leave that group – I have lots of good friends there – the fade only works so far. Having another, unrelated friends group where there’s no chance she’ll show up would be great.

  10. This made me facepalm so hard. I’ve noticed something with men (particularly young men) in the work place is that they inevitably ‘fall in love’ with their female co-workers. Or want to have sex with them. My very good friend recently had her GODDAMNED MARRIED male friend co-worker tell her he wants to sleep with her. And its like, okay fine have a crush, be attracted to other people BUT KEEP IT TO YOURSELF. Where the hell is your brain, fool?!

    The stupidity of men sometimes just astounds me. I just can’t comprehend why they think behavior like this is even remotely okay. (when I say I can’t comprehend yes, I can comprehend it because this is how society raises men and tells them to treat women this way, so yeah I get it, I just really hate it and get the urge to baseball bat people sometimes)

    1. I’m not sure it’s just men. There are people of all genders who have inappropriate work crushes + not so great social calibration. I (cis female) had a big crush on my married boss at one point. To be fair, I did keep it the hell to myself, though. Maybe your anecdata reflects the entitlement of the straight cis man thinking his creepy behavior is harmless.

      1. I agree. I think work crushes, inappropriate and not, are pretty widespread simply because most people spend a huge amount of their time at work, around coworkers. It’s just statistically likely that that will sometimes result in crushes and other kinds of Feelings. And harmless as long as you don’t act on it (or, in workplaces where coworker dating is okay, act on it only in non-creepy and appropriate ways). Most people I know have at least one ‘coworker crush’ story, although the majority of those never say anything or act on it in any way, and usually it’s harmless and blows over without causing any issues.

        I suspect it is more likely that men will express it (and thus result in weirdness and inappropriate behavior), though, because men are more likely to be culturally trained to feel entitled to reciprocation or at least acknowledgment of their feelings.

        1. Also men crushing on women have often been socialized to think that their attention is more important than her job (or anything else in her life) so they will be more likely to act out at work.
          So Many Careers are derailed or ruined by dudes who just can’t keep it to themselves, it’s depressing.

      2. Yeah, I think most of us have experienced innapropriate crushes before. Most of us just understand that we need to keep them to ourselves.

    2. I’ve been thinking about this very thing. Some of these “crushes” have the effect of eliminating competition. A person being chased around their desk at work is not a person who’s able to focus on their career. “But I have Feelings for you!” -As they derail my career?

  11. To add emphasis to the Captain’s words of wisdom: social conditioning teaches men that anything less strong than a clear, unambiguous “no” is actually a “maybe tomorrow” – see a good chunk of TV and Hollywood romances. It also teaches women that you must muddy your statements in case you cause upset; putting the two together results in bad outcomes for women.

    You can’t fix Derek’s side of this vicious social cycle no matter how hard you try; his bad assumptions are outside your personal control. You can fix your side of it if you can find a way to overcome the bad social rules you’ve been trained to use; you can ensure that he’s working with facts not assumptions.

    No guarantee of a good outcome, unfortunately, but it does give you a better chance – if Derek is basically a decent person, a clear no sorts the problem out.

    1. No, even “a clear unambiguous no” is willfully interpreted as a maybe.

      The major reason for saying “knock it off” at the work place, and documenting each time you are forced to say it, is that HR needs it.

      Men are just as good at understanding a soft no as women are. Straight men pretend not to when the subject is sex.

      1. Yeah, the guy who says “I don’t get it” about romance is frequently the guy who can tell you what mood his boss is in by the way she gets coffee in the morning. They’ve just been allowed to get away with “not knowing.”

      2. Exactly.

        Whenever someone implies that they ~just don’t understand a soft no~ or ~just can’t pick up hints, you guys!~, I always look to their other interactions. Same as I do if someone says “I can’t help it, I just say it like I see it” or “I’m just an honest person! I tell it like it is!” or pretends that they’re being an ass because they’re such a brave iconoclast or whatever. Because I only buy those excuses if you also enact that behavior in times and places where your lack of understanding or “brave honesty” hurts you instead of hurting the person you’re talking to.

        And once in a while, yeah, it turns out the person really is brutally and unfiltered-ly honest to their grandmother or to the cops, and once in a while, yeah, it turns out that the person can’t pick up hints or hear a soft ‘no’ from their boss or from that person who they need to provide a good reference. Once in a while, it happens.

        But most of the time, they magically grow the ability to pick up hints/hear a soft “no”/develop a filter/be circumspect in situations where it’s good for them to be able to do so. Which means that when they don’t feel like they have to do it, it’s a choice. They’re choosing to be a blunt jerk or a boundary-pushing jackass when they can get away with it without repercussions. And that’s a very different thing.

        1. “Whenever someone implies that they ~just don’t understand a soft no~ or ~just can’t pick up hints, you guys!~, I always look to their other interactions”

          The captain needs a [like] button. Really. So many times in this thread.

        2. YES.

          And I’ve noticed that most people who genuinely aren’t great at picking up on hints or nonverbal communication or whatever and *aren’t* jerks take responsibility for that, and ask questions or otherwise work to find out what the other person meant rather than taking advantage of the plausible deniability screen.

      3. Men are just as good at understanding a soft no as women are. Straight men pretend not to when the subject is sex.

        This blog post has some interesting data from studies on the subject.

        To quote one of the studies mentioned in the article:

        Drawing on the conversation analytic literature, and on our own data, we claim that both men and women have a sophisticated ability to convey and to comprehend refusals, including refusals which do not include the word ‘no’, and we suggest that male claims not to have ‘understood’ refusals which conform to culturally normative patterns can only be heard as self-interested justifications for coercive behaviour.

        The idea that men can’t understand a soft no is tremendously insulting to men. Men are most certainly clever and observant enough to understand when someone says no without directly using the word “no.”

      4. I wasn’t clear enough, as you’re phrasing agreement with my point as disagreement.

        It’s not that men can’t or don’t get a subtle no – we’re no less capable of getting social cues than women, just as women are no less capable of being brave and daring leaders.

        It’s that men are told that it’s acceptable, even laudable, to wilfully interpret ambiguity in a woman’s “no” as a “maybe later”, by the same sorts of social conditioning routes that tell women that it’s unacceptable to risk hurting men’s feelings – after all, it’s not a “real no”, it’s just you being “coy” or “demure” (can you say “rape culture”? Because, from my male perspective, that’s *exactly* what this bit of social conditioning is). It’s not exactly a modern phenomenon, either – Shakespear’s “Taming of the Shrew” has a certain amount of this in Petruchio’s pursuit of Katherina.

        Now, the social problem is that the more wiggle room there is in the LW’s rejection, the more Derek is going to get a sympathetic audience to his “persistence” from his male friends; in turn, that means that Derek’s desire to “not be a jerk” doesn’t conflict with his behaviour towards the LW. If he’s irredeemably jerky, then yes, no amount of “knock it off” is going to get through; if, however, he has some desire to not be a jerk, then the clearer the “no”, the more his friends are going to respond to the retelling with “Derek, time to move on. Plenty of other fish in the sea and all that”. Combine that with the way women are taught to not hurt feelings, and you have a recipe for trouble, as Derek leans on his male friends to justify his increasingly bad behaviour.

        Now, it’s possible that Derek’s an irredeemable creep of the highest order; in which case, no amount of telling him to knock it off will help – he doesn’t care about “not being a jerk”, and from his point of view, the social convention that a woman’s “no” is actually a “maybe” is a convenient way for him to present awful behaviour to his friends in a form that won’t earn him condemnation [study 1 – trigger warning].

        However, it’s also possible that Derek has, so far, convinced himself that the LW “likes it really”, is being “bashful because ladies aren’t forward”, and thus he’s not a jerk because LW is actually interested, just timorous. If that’s the case, a clear “no” increases the chances that when Derek tries to get sympathy from his male friends, they’ll tell him that he’s deluding himself, and he’ll change his behaviour to stop his friends seeing him as a jerk.

        Ideally, of course, Derek wouldn’t lean on the social convention that women say “no” meaning “yes, but you have to seduce me properly” to justify his bad behaviour – given that he’s demonstrating an inability to manage that level of human decency, the best LW can do is to push on him so that he’s got to dive deeper into that delusion – and then hope that someone *else* is able to spot that he’s developing a serious problem.

        [1] trigger warning – http://online.liebertpub.com/doi/full/10.1089/vio.2014.0022 looks at how the same respondent will deny rape, yet admit to using physical force to obtain sex, and how there are social contexts in which that behaviour would be deemed “acceptable”.

        1. You were clear. I still disagree with you.

          The LW does not need to tell Derek anything for the sake of clarity. Derek already knows.

          The LW may choose to say something blunt, because that may help with HR.

          The LW left zero wiggle room.

  12. The other thing – especially if you’re a pretty non-confrontational person (like I am) is – you don’t have to let the coworkers’ comments that you and Derek “have something going on” go unaddressed. The next time someone makes a you-and-Derek joke or comment, I’d say something like, “Actually, that’s all on him,” or “To be honest, I cringe when Derek flirts with me,” or “Ugh, please don’t say that, I actually find his attention really embarrassing and inappropriate.”

    Then, the next time he does it in front of them, it’ll be much more clear exactly what is going on to all parties involved.

    1. This. Silence is often taken as validation.
      Cut that idea off at the knees.
      “The only ‘going on’ is Derek’s creepy comments, and I’ve asked him to stop it.”

    2. I love that word, “inappropriate.” There are no other connotations associated with it, it’s clear and concise. A short reply containing “inappropriate” is something that will get your message across to anyone who doesn’t already have the full story.

      1. Me too! It hones right in on the behavior without making it personal. As a mom to two young kids, it’s one of my go-tos when someone is pulling down their pants at the wrong time or farting in their sibling’s face.

    3. In the past, I have used “Well, HE certainly seems to think so,” with success. Eye-roll optional.

      1. “Kermit, what’s your relationship with Miss Piggy?”
        “We have a professional relationship. I act professional, she acts like we’re in a relationship.”

        (Read that 20 years ago and still love it)

    4. “It worries me.”
      “I don’t like the direction his texts have been going.”
      “Oh, are you noticing it too? I thought it was just me.”
      “It’s really weird and I don’t like it.”
      “I’m not okay with it actually.”
      “It makes me uncomfortable.”
      “I’m not sure how to get him to stop.”
      “I think he’s into me but I’m really not into him and it’s awkward.”
      “I wish he would stop it.”

      1. These are great. I always found it lower stakes to tell others that I was uncomfortable first. It helped me work up the nerve to be direct with the Main Offender. Not that that’s the ideal order of things, but sometimes it helps to find allies among the enablers.

  13. Even if you happen to be Inappropriate Joke Friends with someone, you get to have boundaries! This is a reconstruction of a conversation I had with one of my very close and trusted friends, redacted because the specifics aren’t really relevant and I don’t recall the exaaact bits of anything but the one that went over my line with him.

    IJF: [gross joke]
    Azz: lol [grosser joke]
    IJF: lol [sexual joke involving both of us]
    Azz: [also sexual joke] lol
    IJF: lol [differently sexual joke]
    Azz: whoa hold on dude, please do not joke with me about me doing [specific act] to you.
    IJF: Oh, ok, you ok there?
    Azz: Yeah, thanks, just that one topic’s a little … you know.
    IJF: Gotcha. [gross joke]
    Azz: ahahah hee [terrible pun]

    And another time:

    IJF: *hilarious mishap*
    Azz: *extensive giggling*
    Azz, to IJF: [innuendo]
    IJF: *extensive giggling*
    Azz, to IRC channel with our closest friends: [innuendo-laden description of hilarious mishap]
    IJF, privately: Er…
    Azz, privately: this bothering you?
    IJF: yeah actually
    Azz: OK, I’ll knock it off

    This friend and I have the honor of being Inappropriate Joke Friends with each other because we trust each other to not go too far on a regular basis, and to knock it off promptly if it becomes a problem. That’s why we’re still Inappropriate Joke Friends, and not That Creepy Suggestive Comment Person I Used To Know.

  14. Are your social gatherings work gatherings, or social gatherings that work and non-work people go to? Because if they’re work gatherings, then I think there’s no reason for your manager to invite Derek. Sure, people who don’t work at a place often get invited along to work gatherings – significant others, visiting relatives, friends you’ll be hanging out with after. Roommates, not so much in my experience. But if this is a work gathering, then your attendance and behaviour has an impact on your work life! Sometimes it’s networking stuff, sometimes it’s teambuilding. But… work gatherings are increasingly part of WORK.

    I honestly think you’re within your rights to talk to your manager (or email) and say “Can you please reconsider inviting Derek to work social events? He makes me uncomfortable. He sends me messages like this *show one of the boarderline sexual messages* despite me making it clear to him that I am not interested or receptive to this kind of attention from him, and now he is at these work gatherings acting like this towards me, too. I don’t want you to intervene on my behalf, but I would like work gatherings to be places where I can spend time with work friends without having to navigate around the creepy friend who doesn’t actually work here.”

    Also… since your manager is young and you are shy, it’s okay for this to be a weird an awkward process. I’ve had to have some conversations of the “I really don’t want to have this talk, but…” variety with my manager. I suggest you open with “There’s something I’d like to talk to you about, but it’s probably going to be weird and awkward.” Awkward conversations happen a lot in workplaces. Being sympathetic and making them productive conversations is part of being a manager, so hopefully he’s had some experience and training on this stuff already.

  15. LW, I want to second the Captain’s advice about telling co-workers the truth about the creepiness they’re noticing. Should this turn into a bigger mess (I hope not) it will be to your advantage to have had one consistent story the whole time. Otherwise it will smell fishy to a person who is trying to get to the truth.

  16. You have said that you are a shy person who is uncomfortable confronting anyone about this, so I would suggest that any responses you plan take that into account. It’s not reasonable to expect yourself to magically going to turn into a no-fucks-given badass of snark, instantaneously, during a time of extreme stress.

    Suggestion #1: Respond in written form. Especially if he is texting you, or otherwise communicating with you in writing. It gives you time to have whatever emotional reaction you’re going to have, and then come back to it once you have thought out what you want to say. It also has the added bonus of being documentation that can be taken to HR if needed, or shown to members of the friend group if you think you need some backup.

    Suggestions #2: If you don’t think you can summon up the no-fucks-given badass of snark for this occasion, try to find someone who can, and let them know what’s going on. Ask them to be your wingman/woman whenever Derek may be in attendance. Hopefully, this will deter him from making comments, but even if it doesn’t, you’ll have someone who can consistently respond with a “Dude, that’s not cool. Can’t you see you’re clearly making her uncomfortable?” even if your involuntary response is to freeze up/giggle awkwardly/politely excuse yourself to the bathroom.

    Suggestion #3: Cut yourself hella slack if you can’t summon up the no-fucks-given badass of snark. Seriously. You are the way you are for a reason, and usually that reason is that women are taught both implicitly and explicitly that they are not supposed to make a scene or cause a confrontation or “stir up drama.” I’m sure that your non-confrontational, shy nature has served you well in lots of other parts of your life, otherwise you wouldn’t be this way. Shy, non-confrontational women still deserve not to be sexually harassed. You are not to blame for Derek’s complete unwillingness to take a soft no for what it is.

    1. Cut yourself hella slack if you can’t summon up the no-fucks-given badass of snark

      YES. This is one of my bugbears at the moment. We can all enjoy the delightful fantasy of the woman (or other marginalised person) who fights back with quips and wisecracks and decisively puts the aggressor in their place. And occasionally real-life examples get shared through social media, and that’s excellent too. But the thing is, those moments are exceptions. and they depend on the marginalised person having a lot of bravery, or other types of social capital, or a real willingness to burn bridges. (And a lot of the time, obviously, we’re thinking of moments in films and TV which are staged and written to play into that “hell yeah” dynamic with no actual risk to anyone.)

      The reality is that creepy people and abusers have a lot of social support and back-up for the things they say, and they rely on that to keep getting away with it. And for all the people who manage a real zinger that puts the aggressor in their place, there are people who try and do it and get punished for it, either overtly or covertly. It’s the same idea as the “woman who fights her rapist”: it’s a brilliant, seductive idea, but then you get people feeling bad for not living up to it, as if patriarchy were caused by women being insufficiently sassy, not by men being gross and entitled.

      So yeah, if you can do a great confrontational response, go you! But there is absolutely nothing wrong with seeking quieter or less visible ways to set your boundaries. You don’t owe it to anyone to provide a spectacle.

      1. Agreed. In some ways it reminds me of the “I woulda” response, where someone recounts something inappropriate or assholish that was done to them and the listeners go “I woulda punched that guy in the nose!”

        Which, a) I’m not sure I believe you, because that’s much easier to say than to do, and b) you know, there are a lot of ways that punching somebody in the nose can backfire, so even if you really would have done it, that doesn’t actually mean that it would have been a smart response. Usually it’s just a way of feeling like an imaginary badass (at the expense of the person recounting the story, who by implication was a wuss for not hauling off and smacking the guy).

        Obviously a quip isn’t as potentially dangerous as punching someone, but the narrative of the clever quip does have a few things in common: it is much easier to imagine than to actually do, it may have unforeseen consequences that are simply not worth it, and its prevalence has the unfortunate tendency to make people who are shy or anxious or even just tongue-tied feel stupid and wimpy for not being able to whip out the perfect response to shut someone down in the moment. If you are the kind of person who can pull out a snappy retort or wisecrack, and it’s safe to do so, then sure, go for it. But the smaller ways of pushing back and setting boundaries are also valid.

    2. Shy, non-confrontational women still deserve not to be sexually harassed.

      This needs to be a poster. Or a t-shirt. Or a coffee mug.
      Hey! 3 for 3!

  17. I’m sorry this is happening.

    My Work Derek was my boss. I sent him an email saying “I need you to stop making comments about (inappropriate topic)” and he immediately apologized and stopped, which was the best case scenario.

    What gave me the courage to do it was realizing that the worst case scenario–getting fired or harassed more blatantly–was clear grounds for a lawsuit. It’s not as clear cut if Derek doesn’t work with you, but I still think it’s worth a shot being direct. A lot of bad things *could* theoretically happen but I think the most likely “bad” thing is that Derek thinks you’re being SOOO MEEEAAN, which is really kind of a bonus if it gets him to leave you alone.

    1. Best Boyfriend just moved to a different group in his job and his first day there, there were ongoing mean-spirited and annoying “pranks” from his new coworkers, which started on April 1st and had not stopped. I asked how his day had gone and he said “Okay except for having to be a major buzzkill on my first day with this team” (because he made it clear he didn’t find such things amusing or cute and refused to be included in them). I said “Think of it as establishing good boundaries from the beginning” and that made him feel a lot better.

  18. I recently had to deal with a (missing stair) Derek at work whose entire conversational repertoire consisted of sexual innuendo. I’d spoken up in a half-joking knock-it-off way a few times, and twice when the specific thing he said was completely out of line I’d told him not to say that. I find confrontation very difficult, but finally reached my limit. I wrote to him, and info copied my sort-of-boss (I’m not an employee, but it’s too long winded to explain the exact set up) advising him that I had already made my position clear verbally, and that the next time he used this language I would be making a formal complaint of sexual harassment to the hospital where we worked and to the relevant professional registration board. I also said that I did not wish to discuss the matter, I did not want an apology, all I wanted was for it to stop.

    I’ve been the target of a vindictive bully in the past, so for the two weeks until I next worked there I was completely freaked out, expecting reprisals and a whole lot of nastiness. I thought through all the derailing ways he might respond and prepared scripts to deal with them. But all that happened was – nothing. As in, normal non-sexual conversation. Bliss. I’m hoping it lasts. I suspect he will try to gradually test the boundary in the future, and I’m not really looking forward to that.

  19. The Captain’s suggestion to use text to say “Stop it” is on point. For shy people, sometimes typing is easier because you don’t have to take the other person’s reaction into account. And if you can’t deal with his defensive, “but I was only joking!” responses, then you don’t have to right now.

  20. I moved from a small town in the south (where the Good Girl pressure is considerable) to the NorthEast, and within a year, into NYC itself. I went from shy to assertive pretty darn fast. (Also had some good teachers.)

    Turns out a lot of shyness is simply lack of confidence and social skills. Both of which can be learned, and both of which are absolutely vital to have: for a good career, to help meet great people, and to get icky people to leave one alone.

    So you might want to explore, at your own pace of course, the great feeling you get when you do draw a line. And defend it. It builds confidence like you wouldn’t believe!

  21. If you end up having a heart-to-heart with your manager/his roommate, keep in mind that people who are inexperienced at being bosses often want to help but don’t know how. Suggesting something specific that they can *do* is a way to help get what you want.

    This is somewhat unrelated, but this is THE BEST ADVICE EVER for dealing with a clueless boss.

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