Tag Archives: Work

Dear Captain, et al, and Awkardeers,

I have searched the archives and not seen anything like my current conundrum.

Cliffnotes: Former partner at the law firm where I am an associate, Jim, left the firm last year. We worked together for approximately a year, during which time he took lengthy FMLA absences. I haven’t spoken to him in the year since he left unless he dropped by the firm to see the senior partner about something. I had heard a rumor Jim was into BDSM, but gave it very little thought. (Whatever floats your boat, no skin off my nose).

Cut to last Friday. He Facebook messaged me asking if he could ask me a question. I thought it would be firm-related, so I said sure. He said nevermind. Two days later, a mutual friend (Sharon) asked if I’d be interested in entering a D/s relationship with Jim. She made the request at his behest, she said. Sharon described it as, “You let someone pamper you and you belittle them.”

I’m not into BDSM, but in my opinion that’s not the issue. This is such a breach of boundaries and professionalism that the more I think about it the angrier I get. We are not friends, we don’t interact socially, and he leaped over several levels of personal intimacy even making the request. Even though Sharon said “Nothing sexual,” to me that’s still a request for intense intimacy.

So, to the question. Do I say something to him? I interact with him professionally now and then. Do I tell him this was inappropriate, rude, and objectifying, or do I write it off and hope it never comes up again? (I told Sharon to tell him “No.”)

– I’m Not Yer “Queen”, Pal

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Hi Captain,

I’m a twenty something female working in a retail job where it’s NECESSARY to work as a team. In the six months I’ve been at my job, I’ve built especially great rapport with a few people. The man henceforth named Paul is one of them. Paul is a year younger than me. Most of our dynamic has been sarcastic banter, punctuated by some more serious conversations about a wide variety of topics. After about two months Paul asked some questions about my opinions on romance related topics (we were off the clock and out in a group with coworkers), and I answered in the context of the happy/trusting/loving relationship I have with my boyfriend of 4 years. Paul seemed surprised to hear about him.

I later brought up one of Paul’s questions I didn’t feel I answered well, and he got extremely flustered and changed the topic. A week later he told me that he struggled with feelings for a coworker at an old job for a year or so before he really stopped having feelings for her, and he regrets that it took him that long to deal with an unrequited crush. Since he told me about that, he hasn’t brought up anything even remotely related to romance.

I’m pretty damn sure that Paul has a crush on me. He hasn’t said or done anything inappropriate either in or outside the workplace, and since describing that old crush has not brought up romance in any context (that was nearly 3 months ago). It doesn’t get in the way of our work, most of the time we still execute the sarcastic banter/serious topics conversations without a hitch.

But I definitely feel like there’s a weird feelings stalemate. In my personal life I would have confronted him about it long ago and let him know that if he can’t handle being around me, then he shouldn’t be around me, and I’d be happy to have his friendship whenever it’s just friendship. But given that we work together that’s not an option, and I don’t know what’s appropriate. I feel bad because I get the sense that he’s doing everything he can to keep the feelings off my radar since that story. If he were creepy I’d tell a manager, and if the fact that we get along didn’t make our job way easier and more enjoyable it would be an unwelcome but simple task to freeze him out. Ultimately I just want to be able to work and occasionally hang out with this guy in group settings without the sense that he’s experiencing heartwrenching crush feels half the time I laugh at his jokes. Is there even anything to do, Captain?

-Midshipman Awkward Sauce

Dear Midshipman!


You’re an empathetic person, so you are putting yourself in his shoes and wanting to make things better, but you can’t fix this for him. Short answer: Say nothing, it will get better soon. “Paul” is actually handling all of this very well, in my opinion, and it would be a mistake to stage-manage his feelings or pry further into them.

He most likely did have a crush on you, he figured out that it would not be requited, and he bailed out just in time before telling you about it beyond an oblique reference to a past situation. Of course he feels awkward, he’s got all these feelings and he can see how very close he came to 1) asking out a coworker and 2) macking on someone who he knows is happily coupled up. I think it speaks to him being a good person that he pulled back when he did. You can help everything get less awkward by being your same basic amount of work-friendly to him and letting him save face. In my opinion, he won’t thank you for addressing it directly: Imagine someone else peeling off a scab that’s on your body, and that’s pretty much what it will feel like for him if you bring it up before he does.

For now, return the text of your interactions to normal relations, ignore all subtext unless it does get angry or creepy or unless he sheepishly confesses, “I was developing a crush on you and that’s why I’ve been acting kinda weird lately” at which point you say “Aw,  knew *something* was up, but I didn’t want to make you more uncomfortable. So you know, I really like working with you and I’d like us to be friends, and I’ll follow your lead on that.” 

Dear Captain,

About two years ago, I was hired to work at an awesome but small non-profit. I spent my first year in a low-end administrative position that quickly became mundane. However, after taking on additional projects and consistently showing my skill and desire for more intensive work, I received a huge promotion to a development position. I now answer directly to the CEO, and things are going pretty well. I just brought a new donor on board, and everyone is singing my praises.

However, a huge mess of awkwardness has arisen.

The woman who held the position before me had years of experience in writing and development. She had a VERY good salary (from what I hear) and was close friends with the CEO. However, her performance was less than stellar. In an entire year in the position, she never brought a donor on board and failed to document most of her contacts. Because of this, the organization asked her to resign early last year. Since I took over eight months ago, I have been trying to fill in the informational gaps. In some cases, I’ve had to start from scratch.

Now, this woman had a list of potentials she was trying to develop, and my CEO (still hung up on how “experienced” she was, IMO) wants me to pursue them. However, I do not know (because of the utter lack of documentation) what the other woman’s relationship to these entities were, and some of them appear to be real long-shots. So now the CEO is asking me to CALL THE TERMINATED EMPLOYEE and ask! I’m so uncomfortable with this request, you have no idea. When she worked here, I was just a low-level associate. Now I’m supposed to tell her that not only have I taken over her old job, I want access to her contacts, too?! It seems insulting. I’m thinking about telling my boss that I just can’t do it. It’s not just an affront to her pride, but also to mine. What do you suggest?


Too Appalled to Call

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A big guy touches a little guy who shrinks away and says "No Touchy!"

Captain Awkward,

I just found your blog an hour ago, and haven’t really found anything fitting my situation.

I have a creepy friend I already turned down in no uncertain terms when asked on a date. I don’t see him often, only every few weeks at work. But he touches me – every time, the whole time. Too-long hugs, rubbing my back, touching my arm, sitting next to me instead of across from me in the cafeteria, and the most uncomfortable of all – saying I love you every time I say something slightly witty or funny. When I used to go after work for food with him and others, he would always pay for my meal. First time I literally did not have enough money for a meal. Every time after he would sneak talk to waiters, or steal the bill from my hand. When I told him I did not like him paying for my food, movie ticket etc, that it made me feel very uncomfortable, he waved it off, saying he was raised this way (What?).

Yesterday he crossed some line in my head. I said goodbye, I need to clock in, and you should go home since you’re off. He followed me outside to the clock in area and just kept hanging out there even though I was technically working. I realized then, he isn’t going to get a clue, and I do not want him to follow me around, touch me, or pay for my food. Ever.

Unlike similar situations I saw you answer, I’m not making excuses for him, I don’t care to keep his friendship if he doesn’t stop acting like this, and while I do think he is just terrible at reading clues I also know he does not touch other girls – or guys – as often or … creepily … as he does to me. He seems very nice, we’ve worked for the same company over two years, but I wouldn’t say I know him well enough to keep making excuses. I Do Not like his touch, and WILL tell him to stop.

I need advise on HOW to tell him to stop. He didn’t catch the subtle clues of shifting away from him, never initiating any contact, and tensing up whenever touched. I don’t care one way or another about losing this “friendship” but I do care about how this future conversation will get around to the rest of my co-workers, and how THAT will interfere with doing my job and the social situation there.

I am sick of worrying that he will be working the same shift as me, and need help on how to say something without being my normal blunt-edging-into-mean-self.

Desperate for advice,

Stop Touching Me

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Greetings Captain!

I’m having a hell of a time trying to decide what to do with my life. I would like a career that suits me, but the problem is I have no real skills.

Some backstory: I graduated with my BA in 2011 from a small school that no one has ever heard of. My degree is basically useless and no one takes it seriously. After attaining my BA, my passion for the subject is virtually non-existent. I tried everything I could think of to get started in my career at that time: internships, networking, attending conferences, etc. Nothing worked. I would like to go back to school, but after having such a negative experience with my current degree, I’m terrified that it will happen to me all over again. This is going to sound pretty weird but, if I went back for a second degree, I’d probably go for a law or film degree. I am very passionate about both subjects.

Unfortunately, I’ve had many people tell me that going back to school is a horrible idea. They are probably right because I would have to pay for everything out of pocket again (I’ve never been eligible for any grants or scholarships despite graduating on time with honors.) Something keeps pushing me to try though. I’ve visited numerous colleges over the past few years, I even got close to going back for my master’s. But every time I am about to pull the trigger, I freeze up and the doubt creeps back in. I fear that maybe I just don’t have what it takes anymore.

My only bankable skill is my ability to communicate with just about anyone. This led me to take on retail/sales jobs for eight years which I hated immensely. My current job is very demanding and I work 50-60 hours a week, but I am NOT going back to retail. I would love to just start over somewhere new and have no issue with relocating. However, my fiancé’s career here has really taken off and we can’t leave just yet. Besides, where would we go?  I live paycheck to paycheck now because I don’t have the qualifications for a better paying job. I doubt I could attain a better job elsewhere until I have more education/experience.

So I guess my ultimate question is this: what skills have helped you the most in your life? What would you recommend to someone who is super lost and doesn’t know how to continue? What steps should I take to build up my qualifications? How did you decide which steps to take in your life that have led you to a successful career?


Mad (that I have no) Skills

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Hi Captain,

I could really use your help with a situation I’ve been dealing with at work. My job is at a small marketing firm, and I have a lot of daily contact with our customers, both over the phone and by email (not in person). One of our customers, whom I’ll call Jim, has always been a bit of a weirdo. He has a tendency to get hung up on small details that are really unimportant, so he’s much “needier” than most of the people we serve, and everyone in my office suspects he has some sort of neurological or mental health issue, based on the way he communicates. For instance, on the phone, he’ll say one thing in a very friendly, “normal” way, and the next time he speaks, his voice will sound completely different and curt, almost as though somebody else has picked up the phone.

Anyway, my co-worker “Lindsay” and I have worked with him on a couple of projects since I started working here this spring. Recently it became apparent that he was getting us confused, probably because we have similar job functions and will trade off on work, and because we are both female and might not sound that different over the phone. At this point, Jim went and found pictures of both of us on the company website and saved them onto his computer, so he could “tell us apart” (which makes no sense, since we’ve never met). He also sent me an email individually telling me I was pretty, and he should have guessed, because I “sound so pretty over the phone.” He also emailed Lindsay and I jointly to comment on our appearances, and included winky faces and LOLs and the like which were not the norm for the professional tone we like to take in our emails. My (male) boss initially offered to speak to him about it, then changed his mind and said he’d let us decide how to handle it. We both ignored his emails and hoped that would be the end of it.

He called me earlier this week and immediately told me he was smiling because he had my picture up in his email and was looking at my pretty face. I completely ignored this comment and asked him a business-related question in a very serious tone, but he kept up the flirty comments throughout the call. Because I was flustered that he did not seem to understand professional boundaries, I could not think of anything to say to change the tone of our conversation, and giggled nervously a few times, which probably did not help his apparent impression of my willingness to participate in his flirtation. Now, every email that does not CC anyone within his own company is filled with the LOLs and declarations of how he “lives for working with [name of my firm].” I feel that each passing incident makes it that much harder for me to speak up and put him in his place. I dread talking to him.

My company is tiny, tiny, tiny, and we do not have HR. I have documented each of these exchanges, and have joked around about it with Lindsay and my boss. Now I don’t feel so jokey about it, I want it to stop. I think my boss could still address this for me, but I would much rather try to take care of it myself first. At this point, I’m at a bit of a loss, especially since the guy can be so Jekyll and Hyde, and was already weird to work with before he started with the creepy comments. Any ideas for me, that would minimize any damage to the business relationship? I’m not sure he’ll stop even if asked to directly, so I’d love some follow-up lines to reinforce my boundaries after the line is drawn.

Thank you so much for your advice. I wouldn’t normally be this shy about telling someone to STFU, but I’ve never had a customer get creepy with me before, and it’s obviously different than a random creeper encounter on my personal time.

Sign me —

My Appearance is Irrelevant

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Hello everyone! How are you? I am completely destroying my cat’s sense of safety and object permanence packing up my entire apartment for a move this week. All the comments in the spam filter are actually spam, so it must be time for another question. Shall we continue the Labor Day holiday with a work topic?

Dear Captain,

I have worked in my office for 8 years. My colleague has been here over thirty. He’s in his sixties, I’m thirty. I thought he was one of my best friends though we’ve had our issues before. Let me explain. No, there is too much, allow me to sum up.

We do the same job in a support team. For a long time, I’ve been taking on more stuff because I’m asked to (and because I actually like to feel like I’m doing my job to the best of my ability) and he’s been excluded somewhat from tasks he likes. I don’t know why this is – it’s certainly not my doing or responsibility, but the digs he gets in makes it clear that he thinks I take everything on (I can be prone to this and work against it…) and it’s basically my fault and there’s a giant conspiracy against him. If there’s a conspiracy against him, I’m not part of it. Which I’ve said a million times.

Sometimes the way he talks I think he has absolute contempt for me. He doesn’t like me being bossy (who would?) but he doesn’t pull his weight or step up to the plate to *offer* his services. The number of times I’ve walked past his desk and he’s just on the internet… or sometimes reading the newspaper! I’ve not said anything to our boss because I don’t want to get him into trouble… and because I feel it would make things worse anyway! All this, incidentally, while I’m tearing my hair out trying to get things done by deadlines etc.

I feel like what he wants is for people to go to him and say ‘Will you do this/help us with this?’ but he won’t offer, won’t put himself forward. When people do? He’s grumpy with them. So more and more people come to me because they know they’ll get a more positive answer… and he doesn’t really keep himself up to date with changes so oftentimes can’t answer their questions anyway!

He sits grumbling that he never gets asked to do things/attend meetings/whatever but when he IS included he then complains that he just sat there useless! All the while, getting in digs at me. He says he can’t be bothered fighting my ‘need to have fingers in all the pies’, to which I have responded that I don’t want fingers in all the pies (i’m inquisitive certainly, but I truly don’t feel that way, but it seems to go that way mostly because he won’t step up and because there’s nobody else). I try to fight the urge to do everything and I thought I was doing much better with trying to spread the load. Apparently not, or not enough/in the right way for him.

Have I mentioned that no matter how I approach things with him, he always seems to interpret what I say or do in the worst possible light? In fact, I do most everything with a view to not upsetting him, not making him irritable or grumpier…. which often means not even *ASKING* him to help out with things because a: I know he will just say no and b: he’ll accuse me of being bossy… then he gets angry because he sees ‘me doing everything as ‘him being left out’.

And all the while he’s sat there saying he doesn’t want to be there/wishes he didn’t have to work in this dump anymore/doesn’t get how *insert project here* works.

So I feel constantly like I’m on eggshells with him. And if he’s pissed at me, he’ll be nice as pie to everyone else and speak to me in monosyllables, which makes me feel about two inches tall.

Last year, he complained to our manager about me being bossy and know it all and opinionated, I think… and at the time I basically apologised, said I’d do better, and didn’t go back with my laundry list about him because I will always assume that I’m in the wrong. It was only later that I thought ‘hang on a second…’

I KNOW I can be bossy, especially when I’m stressed myself. I seem to construct everything at work around a fear of screwing up, which isn’t exactly healthy, so when it’s very busy or I feel like everything’s on me, I do get anxious. Since the last run-in, I’ve tried REALLY hard to regulate my weaknesses. It seems he doesn’t care/hasn’t acknowledged this. I can’t help wondering now that it’s not that I’m patronising/condescending/bossy, but that he will always interpret it that way because he chooses to. But I don’t know because my mind is being yanked in a million different directions and now I’m terrified that everyone thinks that I’m those things as well.

We’ve talked about all this before. I’ve tried to stress to him that I’m never looking to do things to make him feel bad, that I don’t do anything with a mind to making his day worse. I’ve also said that he needs to be direct when he feels I’m doing those things… but he does the same passive-aggressive thing as always.

I deal really badly with passive-aggression (see also: my mother). I know this. I try to do better. I am trying so hard to be the best human I can be and it just seems like it’s all for nothing. I do not know what to do, how to approach any of it!

I don’t feel I can talk to him because he’ll blow up, so I sent him an email trying to explain my side as gently and yet as honestly as I could. He came back and said my email was condescending, that he is way more productive when I’m not there… I just wanted to be honest for once and got accused of condescension, being confident/rude/pushy.

I don’t know… am I a mean bitch, or is it that he won’t accept anything but the responses he wants?

I have no idea what to do, Captain. I really don’t want this to be a thing with our manager again, or to affect my reputation with other people at work – if it hasn’t already – and I’m also scared that actually, everyone else thinks I’m those things when I really try not to be and I’ve been trying so f**king hard to regulate my lesser demons.


Terrified Yet Increasingly Unwilling To Be His Doormat

Dear Terrified:

The fact that you are walking on eggshells around this person and signing yourself “Terrified” is giving me a lot of information. That information sums up thusly:

  • Whatever bond you shared in the past, your coworker is now actively sabotaging you and your work.
  • He wants you to be scared, miserable, and walk on eggshells.
  • I don’t think there is a fix where you guys are friends again, so what we are going for is neutrality and distance.

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