Dear Captain Awkward:
I have a really great job; creatively fulfilling, changing and full of new challenges and people. I’ve been in this job for a lot of my 20’s, and devoted a lot of time and emotional energy to it.
A lot of the greatness of the job is down to my boss. So far, I’d say our relationship has been warm, informal and rather protective, but professional. However the other week (after an work event we were attending together) it became so warm and informal we drunkenly made-out.
He kissed me, not that I’m looking to assign blame, but I was definitely into it. And it was a mess, and kind of innocent, and he’s my boss, and married.
Backstory; while I don’t really identify as asexual all signs so far point to me being somewhere down that end of the ballroom. I’ve had crushes on one or two men (maybe even been in love) but have had very little romantic or sexual experience. I’m basically okay with this, as I experience attraction so rarely (and it’s my body and I’ll do what I like with it, even if that’s nothing) .
However since that night I’ve been left feeling lonely, and touch deprived. I wouldn’t truly say I have a crush, but I want his attention and affection. I feel very safe with him and if he was any of my other friends I’d be asking if he wanted to do it again and working out whether it could be a thing. As it is, we very quickly went back to normal, which is right but has left me so at odds with myself.
How the hell do I behave, now I’ve finally noticed I’ve been having this weirdly intimate working relationship? I feel like such a loser for being so affected by a drunk kiss but really my problem is that I feel like I don’t know myself at all. How can I try to be happy romantically in the future, when my sexuality is such a small, hidden thing?
Thank you, I’d really love to have the chance to think about this anonymously. As it’s pretty professionally compromising I feel I can’t talk about it to my usual Team Me!
Dear #610 (for lack of a better sobriequet):
I wish your boss would apologize to you and THEN go back to normal, like, hey, that was out of line and gross of me, I’m sorry, let’s please go back to normal. Married older dude, young employee, him initiating the kiss = he is the one who is out of line and the one with responsibility for resetting or redirecting things. He is the one who should feel weird right now and be worried about what you’ll do and say.
In the meantime, normal and professional is good. I don’t think you got profound information about this dude and how he is special. There’s something I see sometimes from folks who experience attraction rarely, where if they do, they think that it must be somehow extra meaningful. “I felt The Thing, so this must be A Thing! It is a sign!” That does not necessarily follow, so be smart and let Time and Normal do its work to disengage you from this crush.
I think you got some information about what makes you feel attracted, that does not have to be acted upon and you got some information from yourself: “Hey, #601, it’s me, your Body! We’ve got pleasure centers we’re not using. So, I dunno, maybe think about how to go about meeting someone to make out with who isn’t your boss? Someone from the Legion, Dude Division, perhaps? Or maybe we can visit the non-skeevy neighborhood sex shop and spend a little quality time together, alone? Boss is nice and he smells good, but you might want to talk to Brain about whether we get drunk around him from now on. I mean, I’m down for whatever, but I’m not the only driver of this bus. Okay, we’ll talk soon!” Listen to Body! Look into lots of ways to touch and be touched and love your body. Hug friends who are down for it. Get a massage.
You’ve got this! It’s going to be fine. Unless he keeps kissing you, in which case 1) ask him to stop and if he doesn’t 2) report his skeevy ass to HR.
Dear Captain Awkward:
So, extremely awkward situation here: my boss came on to me. AWESOME.
He’s a married guy in his forties (I’m female and 28), and I work very part-time for/with him, mostly independently; we meet once a week in a tiny office, just the two of us. Which usually ends up being half just hanging out–I’ve considered him a friend as well as a boss, and I know that he has considered himself my friend *more* than my boss. It had vaguely occurred to me that he was probably a little attracted to me, but I didn’t think of him like that AT ALL (older men=no, boss=NO) and assumed that if so, he would keep it under wraps.
Well, today, he confessed to spending a certain amount of constant energy refraining from kissing me. I was all, “…well, thank you for trying?” at which point I now see that I should have LEFT, but I didn’t, and then a few minutes later he actually went for it(!!). I turned away, said no, and he backed off, and I was all, “Let’s keep this platonic,” and he agreed, and then I left.
So…now what do I do? I don’t want to quit, although I could without major financial crisis. I still like him as a person. But I’m not 100% convinced he won’t ever try again (though I am sure he’ll take no for an answer again), and I DON’T WANT THAT. I can’t control his feelings or actions, so as best I can see, my options are, 1) quit, 2) never bring it up again and keep the office door open when we have meetings (maybe wear shapeless clothing? today I was in a short skirt) and…hope it doesn’t happen again, 3) bring it up again to reiterate that my feelings on this matter are NO. Except I don’t know what I would say exactly, when I would say it, and how often it should be repeated.
Relatedly: this is not the first OR the second time an older, male, MARRIED friend has expressed a long-term attraction to me. I hate this–I don’t think I’m doing anything to express that feelings like that are welcome! I’m not at all flirty with them, I don’t think(??). I don’t date much (quoth older, married, attracted friend: “I just don’t understand why not!”) but being perpetually single is not a “male friends welcome to try it out!” sign, ESPECIALLY WHEN THEY ARE MARRIED. If you’re attracted to me, that is YOUR and YOUR MARRIAGE’S problem, not mine! There’s probably nothing I can really do to keep this from happening again, but if you have any suggestions, I welcome them.
Dear Not Interested (#611):
What some people in your shoes do is to pull way back on the casual/hanging out/friendly vibe and stick only to work topics. Boss: “You look very fetching today, I almost can’t keep from kissing you“/”Wow, that makes me very uncomfortable. So about the project…” Yes to keeping the office door open. Yes to avoiding personal topics of conversation.
You might also want to address it head-on. “Boss, I like working here, and I want to keep doing so, but I am feeling very uncomfortable after the last time we talked. I do not want to discuss or deal with any romantic advances at work. Can you promise me there won’t be a repeat of the other day? If so, I promise to put it behind us and focus on work. If not, I need to start looking for a new position and wrapping up my duties here.” Of course, he should be the one doing the work to set you at ease, but if you have to do that work, be clear and specific.
You should only have to say this once, ever. If he keeps pressing and gives you puppy dog eyes, RUN. If he acts like you are making a big deal out of nothing, RUN. Also, if you do start looking for jobs, have a trusted friend call to “check your references” and verify what he’ll say before you give his info out to future employers. Not everyone can afford to just GTFO, so if you can, enjoy that freedom.
I need your help; I’m trying hard to keep to the word limit, so I hope I don’t lose too many salient points.
I’m massively attracted to my boss, possibly in love with him. I think he feels the same way. We work brilliantly together, but our relationship is distinctly non-bossly. We flirt constantly in the office, when we go to bars people assume we’re a married couple. Half the office thinks we’re engaged in a secret romance (we’re both single, and age appropriate) and the other half thinks we’re just hilarious jokers.
There was an escalation last weekend. After work drinks led to dinner which led to a massive fight about nothing (well, my jerkbrain probably arguing because WHY DON’T YOU JUST KISS ME NOW) which led to apologies and hugs, more drinking, more physical flirting, me propositioning him, him asking me to dance, and eventually him basically running into the night sans me saying he had to be “appropriate”.
The next two days in work were awkward in the extreme, but the subsequent three featured massive flirting escalations as if last week didn’t happen.
I HAD been wondering how to tell him soberly that I fancy him and want to know if his strange behaviour is because he doesn’t feel the same way or because he DOES feel the same way but he’s my boss . . . but now unfortunately I think I need to tell him I’m resigning.
I have a job offer pending. I could have a relationship with this guy while working for him (not strictly prohibited, and there was a similar situation years ago with others that had a happy ending), but I don’t think I can continue to work for him if we have The Talk and he says he’s not interested in me.
But I also REALLY don’t want to frame this as “if you don’t date me, I’m resigning”.
So, when my offer is firm so I can make an escape if I have to, how do I tell him I’m attracted to him, I would like us to give a relationship a go, I would be willing to change jobs to facilitate it . . . but if he says no I want to leave anyway? How does it even make sense – I love you so much I’m willing to damage your business and go work for one of your rivals? Is there any way for this scenario NOT to be ugly?
I don’t want to pressure him into a feeling of – date me or you lose your right-hand-woman. Feels rapey and disrespectful. Equally though . . . I don’t think I can stay as his right-hand-woman and not act on my pants feelings.
So – help?
Not Dating My Boss Yet
Dear Not Dating (#612):
All the bosses from the other letters just read this and did a fist-pump. THERE IS HOPE, they said. NO, I say.
Would the new job pay you more? Give you a better title, an increase in visibility and autonomy? If you didn’t have feelings for your boss, would you want to take the job or is this something you are considering only out of FEELINGS?
Your boss knows you’re attracted to him. You propositioned him. He ran into the night. There was, I believe, Dirty Dancing. It’s not a secret.
If the other job is something you want, one good possible move is to take it without fanfare, give your notice WITHOUT having any talks about feelings, wind up your work in a competent and classy manner, and keep in touch professionally and personally afterward. This is the position that gives you the most financial and personal power and autonomy. If the feelings are there, and you leave on a good note, you’ll both figure it out eventually and your coworkers will be relieved when the Boss-And-#612-Sitting-In-A-Tree Comedy Hour and Variety Show goes on hiatus. Or, clear the air with a frank personal talk, pull back on flirtatious behavior at work and give him a lot of space, and keep the other job offer quiet/stall while you figure out the interpersonal shit. If you want to have a discussion, ask him to hang out away from the office and lay it out there:
“I want to apologize for my inappropriate behavior the other night. It’s not a secret that I’m into you, and I’d like us to possibly date. But I don’t want to just accident into it, and I definitely don’t want to drunkenly flail into it or make you feel uncomfortable. What do you think about that?”
He’s going to say whatever he’s going to say. If he says “No, I’m not interested” you say “Well, thank you for hearing me out, I had to ask and try to clear the air” and then get out of there as soon as you can. Go home, think about things, maybe take the new job, maybe stay at the old job, pat yourself on the back for being up front and brave, but do NOT initiate flirting with that dude again in this lifetime. If he says “I really am into you too, and I’d love that, but Work Stuff” then you have an opening to say “Well, if I left the company, would that make you feel better about going on a date with me?” or “Do you think there is any way we could work out a professional arrangement that makes us both happy, like, maybe moving me to another team?” If he says yes, or maybe, or seems otherwise positive, then I think you should go home and think about the other job offer and what it is you really want to do, because his saying “sure, if you left I’d consider it” does not constitute any kind of bargain. If you show up the following Monday and blindside him with “I QUIT, WOO, WE CAN DATE NOW” you might get a whole lot of “Yeah, so, about that….”
This is why boss-employee dating can get really gross, really fast. To be in the best negotiating position for yourself professionally, you should raise the other offer with him at work, in a work context, and discuss it like work people. “Boss, I’ve had another offer from company x. It means $y more, and a better title. If you could match that and also agree to (other thing you want) (like, working from home a certain amount or increased travel or a better computer)(NOT “YOUR SWEET LIPS ON MINE”), I’d consider staying. I have to let them know by x day.” To be in the best negotiating position for yourself personally, you need to be able to find out “do you like me that way and want to do something about it y/n” without the threat of “Or else your team will be left in tatters! MUAHAHAHAHA” pressuring the decision. What you don’t want to do is stay in a situation you are ready to leave because of vague promises, or have a romantic partner sacrificing your interests for those of the company.