What to do about my months-long crush on sweet nerdy volunteer supervisor?
October 22, 2010 10:39 PM   Subscribe

I'm female and in my late 20s. I started volunteering at a local bookstore about eight months ago, and I've had a major crush on my supervisor since the very first day. It started as just a mild heart-skip, but as the weeks passed I found myself liking this guy more and more. He's got this reserved yet friendly geeky nature that I just can't get enough of. Oh my.

I thought there was a little spark between us as well. He used to come into the area where I was working and ask how I was doing, which is normal, but then he'd just linger around me for a bit like he didn't want to end the conversation. Once he approached me after work just to show me a research website he knew I'd like. Sometimes he'd just come and stand near me for no particular reason. So I started wearing the tiniest dab of perfume behind each ear, hoping he'd notice. No comment, but once he rested his arm on my armrest (touching mine!) while he was checking my work. And once, when I asked him to look up a little info about a local event I was interested in attending, he literally printed out the whole website for me and put it all into a neat packet with a big paperclip.

But then everything seemed to change. I sent him a Facebook friend request, which he accepted, but he never visited my profile or replied to my one short, friendly post on his wall (and never saw the PM I sent asking him out). He'd told me he rarely checks his FB, but you'd think he would if he just added a girl he liked, right? On two separate occasions I've offered to share my snack with him, but he declined both times. When I leave him a work-related phone message or email, I'll occasionally include a friendly comment or joke, which he completely ignores. Then there was this whole awkward time where I wouldn't talk to him, and he wouldn't talk to me, either.

And just when I think all is lost, he'll show up unexpectedly with a little treat for me from the upstairs office, or ask me about something that recently happened in my life, with that sparkle in his eyes, and we'll talk for a bit. I told him I've got the Sims 3 on my phone, and he said he likes the Sims too. But these little interactions have been happening less and less. Some days he won't even talk to me at all. I know the bookstore's a busy place, but still.

Yes, I have considered the possibility that he's gay. But here's the thing. We work in one of the most open-minded areas of the entire country. Also, while talking with him one-on-one, I've casually dropped the fact that one of my parents is gay. So if he's gay, why hasn't he taken these little opportunities to come on out? Most recently, I asked him privately if there was anything I'd been doing lately that was bothering him. He looked utterly surprised and said no. This is all very confusing.

So what to do next? I don't want to risk my volunteer position in any way. I do good work for the store, and I'll be there at least until next spring (when I'll have a full year of solid experience for the upcoming job hunt). By the way, this guy is worth it!
posted by tamagogirl to Human Relations (38 answers total) 4 users marked this as a favorite
Have you asked or otherwise gleaned if he's actually single or not?
posted by cmgonzalez at 10:46 PM on October 22, 2010 [2 favorites]

It seems to me like he's keeping an appropriate employer-employee relationship going. I don't know what else to say about it. It is what it is, exactly like you describe it.
posted by sanka at 10:55 PM on October 22, 2010 [5 favorites]

Some people *really* don't check Facebook that often. I added my friend's husband, who just made an account, and she had to go in and accept all his friend requests (he couldn't figure out how) and he hasn't even logged in since.

As for sharing a snack, some people have germ issues too. And really it seems like either he is just trying to keep it professional, or he doesn't want to make a mistake and take your friendly gestures as a crush (because for all he knows, it's just friendly and nothing more). But I'm leaning towards the former.

tamagogirl: "once he rested his arm on my armrest (touching mine!)"

I know, personally, how this makes your heart race, but he is probably clueless that he was touching you.
posted by IndigoRain at 11:10 PM on October 22, 2010 [1 favorite]

Ask him out.
posted by phrontist at 11:11 PM on October 22, 2010 [2 favorites]

For goodness sake, screw your courage to the sticking place and ask the guy out for a drink or whatever, rather than parsing the number of times he blinks when talking for ridiculous clues about whether he likes you or not. There is an easier option!

You're in your late twenties, come on. Just do it. There are only 3 options:

1. he says no.
2. he says yes, but it's clear it's just friends.
3. he says yes, and it's clear he's date.

Be prepared to give up being a volunteer etc. Sleeping with your boss is never a good idea, but having 6 months volunteer vs 12 months or whatever is not a big deal.
posted by smoke at 11:25 PM on October 22, 2010 [2 favorites]

Cowgirl up and ask the guy out, in a way that's clear and unambiguous. ("Date with me?" is ok; "Hey, there's a thing, never mind, but maybe, anyway" is not ok.)

And like Smoke says, if you do ask him out, that may mean the end of the volunteer gig. But that's ok -- there's a ton of places to volunteer.
posted by Forktine at 11:34 PM on October 22, 2010

Response by poster: smoke: Be prepared to give up being a volunteer etc. Sleeping with your boss is never a good idea, but having 6 months volunteer vs 12 months or whatever is not a big deal.

Thing is, I've been doing a lot of work on a special project he supervises. I think this project is important too. I wouldn't want him to lose me as a volunteer if I asked him out and things got awkward.
posted by tamagogirl at 11:37 PM on October 22, 2010

Well then don't ask him out! lol, this isn't really that hard.
posted by smoke at 11:40 PM on October 22, 2010 [8 favorites]

If asking him out would potentially jeapordise the project, then you need to decide which one's more important. If the project is, then why bother trying to decipher every innocuous comment or gesture he makes? If the project is not, then asking him out is a nice and clear way to figure out how he feels.

This kind of intense introspection and replaying of the past is a kind of narcotic - it's easy to become completely enthralled in this kind of stuff, but you need to quit it if you want things to progress at all.
posted by twirlypen at 11:49 PM on October 22, 2010 [3 favorites]

I honestly (sadly) don't see anything in his behaviour as you describe it that would suggest he was flirting with you - it all seems like totally normal, friendly behaviour from someone you work/volunteer alongside. It's easy to interpret that otherwise when you're in a crush-cloud of romantic optimism. My guess is that he did see the PM you sent him asking him out and that was the first time it occurred to him that you felt that way, and that's why he stopped being so friendly, because he didn't want his behaviour to be misconstrued.

However, I wasn't there and didn't see the sparkle in his eyes when he asked you about stuff, so I might be wrong. The only way to find out for sure is to ask him out. From what you've said he is not, really not, going to suddenly turn round and ask you on a date without prompting.

But as others have said, he may very well decline so weigh it all up first. If you really want the volunteer gig without awkwardness you might just have to resign yourself to enjoying the crush inwardly until you can someone else to your attentions on. (Rider: I am single, so what the hell do I know about rash romantic gestures?!)
posted by penguin pie at 12:04 AM on October 23, 2010 [5 favorites]

All the things you have mentioned seem infinitesimally small. Tiny dabs of perfume? A printed out website? Friendly chat? Yawn! Has he ever actually flirted with you?

Figure out if he's single. If he is, ask him out. Make it clear that it's a date. People are often completely oblivious that they are attractive to others. If he's gay, he'll say "I'm gay" and that will be that. If he doesn't want to mess with the work relationship, he'll say so too. Don't keep fluttering your eyelashes praying that he'll notice you've got it bad for him; he'll probably think you have an eye infection instead.

He understands that you're working closely with him on this special project. If he has the same fears as you, chances are he'll either voice them or cross that bridge if you come to it. Either way it's the same agreement of risk that you'd be making.

Also, a lot more people than you might think give not one single damn about facebook. It seems like some folks think it's imperative and vital and central to their very existence, but facebook is truly a non-entity for many. I doubt his inactivity on his account says anything one way or another.

Flirt with him directly, on a break or something, ask him about a girlfriend (you can frame it in terms of "so how's your social life, seeing anyone lately? I've been bored out of my skull!"), and ask him out. Or don't, if that's not your priority. Just stop this introspection and inflation of tiny gestures so you can get on with it, already.
posted by Mizu at 12:07 AM on October 23, 2010 [6 favorites]

I think sanka's right. He may like you, but be wary of the appearance of impropriety.

I know for myself, work now can be awkward at times after having incessant sexual harassment training pounded into me for ever and ever and not having been accustomed to working with women. I've probably seemed stand-offish to people at times because I just refuse to go down that "she's cute" or "Hey, I like her" line of thought. Work's work.

Even without the employer/employee thing thrown in there he may be overly sensitive about being Mr. Creepy. We reserved yet friendly geeky guys can find it easy to imagine scenarios where you are just being friendly, but don't mean that.

Adding in the fact that I'm your supervisor, yikes. I'd probably need you to be more blunt and just ask me, because I'm sure as hell not going to initiate anything. Not that I wouldn't accept the offer, just that I'm not really in a position to guess wrong and make things weird.
posted by ctmf at 12:42 AM on October 23, 2010

If someone inspired me to write a question like that I'd just bite the bullet and ask them.
posted by Biru at 12:52 AM on October 23, 2010 [1 favorite]

I have been in a nearly identical situation (see my first MeFi question). I volunteered at a bookshop & had a massive crush on my manager. I also thought there was a bit of a spark, and couldn't figure out what was going on. Turns out he had a girlfriend; we were FB friends, but she had asked him not to add their relationship, so I had no idea. Also, he almost never uses FB.

What happened in the end? He and his girlfriend broke up, and I am now the girlfriend. :) We've been together 18 months & I'm looking forward to lots more time together. I still volunteer at the shop, too.

However, due to the supervisor-volunteer situation, I would wait until you're a bit closer to leaving to make it less uncomfortable for him. Going out with a volunteer would obviously have huge ramifications for him professionally. I know it was a massive leap for my guy, and I think in the end he only asked me out because I was leaving in a few months.
posted by bibliophibianj at 1:23 AM on October 23, 2010 [1 favorite]

Oh, an addendum: Don't be miserable if he does have a girlfriend, but don't assume he'll break up with her for you! I very seriously doubt that my situation is representative, and I'm not the reason they broke up, anyway.
posted by bibliophibianj at 1:28 AM on October 23, 2010 [1 favorite]

Ask him out, but in the British way. We do that by asking people out without "asking them out". Say to the room in general (with him present, of course). "Damn, I feel like a drink. Who's with me?" If he has any interest in you he'll accept. Maybe some others will too, maybe they won't. Either way, you've broken the ice and once out you can do the whole socialising/getting to know you outside work thing. If that goes well things should flow. If it doesn't, or he doesn't agree to go out with you in the first place, well... you gave him the chance.

This is what we Brits do instead of "dating", which we don't understand at all.
posted by Decani at 3:05 AM on October 23, 2010 [22 favorites]

It doesn't sound to me like he's interested in you at all. No offense. The examples you've given don't sound like anything more than a nice person who gets along with a coworker in a friendly but professional capacity. It's also funny that "maybe he's gay" was the first possibility rather than "he's got a girlfriend" or "he's just not that into me." If you really want to find out (and you're not going to be able to stop thinking about him without knowing for sure), ask him if he wants to grab a drink after work- if he accepts, hey, maybe I'm wrong and he is interested, but if he says no then you know he's not but there won't be any awkwardness because a suggestion of hanging out after work definitely opens a door to future interaction but doesn't scream Massive Crush.
posted by emd3737 at 3:20 AM on October 23, 2010

There are several guys at work whose behavior seems to be like this towards every woman within 40 years of their age who roughly equals a colleague. Confused the heck out of me when they did it to me at first, since I knew from their insurance records (as an HR person) how many dependents they have. I've met most of the wives and girlfriends now, and it seems clear: the high school/college definition of "OMGosh he is sooo into you, swoon!!" overlaps noticeably with the grownup "how male and female colleagues treat each other when they're being nice."

You should wait till your volunteering time draws to a natural close and then, if you still have the crush, ask him out. You don't have nearly enough evidence to risk everything, IMHO. However, I also think that "fortune favors the bold" was written by a freakish statistical outlier, and am incredibly risk-averse.
posted by SMPA at 5:58 AM on October 23, 2010 [3 favorites]

The thing is, we all estimate how "awkward" things will be from the standpoint of how it would feel if the person said no. That moment is definitely an ouch moment. But it is hardly a level of awkwardness that will continue. It wil hardly "jeopardize the project."

So ask him if he'd like to go to dinner.
posted by Ironmouth at 6:00 AM on October 23, 2010

It doesn't sound to me like he's interested in you at all.

I wouldn't worry about this. He doesn't have to be interested in you now at all. He might have never even thought about it, but would be interested once he learned you were interested.
posted by Ironmouth at 6:08 AM on October 23, 2010 [3 favorites]

How do you know he never opened your message on facebook asking him out?

I am in the "this is a guy upholding a proper employer/employee relationship" camp.

Ask him out in person. Be brave!
posted by morganannie at 6:17 AM on October 23, 2010

Having been in this situation before, I vote that he is kind of interested, but has a girlfriend/is also interested in others. Of course, I don't actually know.

How about flirting with some new guys?
posted by bearette at 6:46 AM on October 23, 2010

Since he is your supervisor, he is probably aware that asking you out might possibly be illegal if taken the wrong way, and could lead to a career-crushing lawsuit.

Your move.
posted by musofire at 7:19 AM on October 23, 2010

I think you have to decide whether you like your volunteer position or him more. If you like him more, then ask him out. If he says no, then that's that. Sad, but you're young.

If he says yes, then you discuss the legal niceties with him. If he says dating an underling is out of the question, then quit.

If you're not willing to quit your volunteer (!) position in order to date this guy, then you're going to forget him pretty soon anyway.
posted by luke1249 at 7:32 AM on October 23, 2010

"Ask him out"? She already did ask him out. He ignored her message. Probably because he's her boss.

I wouldn't assume he never saw your message. I would assume he did see your message and wasn't interested.

As long as you're still working for him, just leave this alone.

However, you can't dismiss the possibility that he's gay. I've been in super-liberal towns, in gay-friendly social groups, with discussions about gay people and/or gay rights, talking to someone who notably did not volunteer "Oh, I'm gay" -- and I only later found out they are. Sure, some parts of the country are more accepting than others, but I don't think there's any part of the country where all the social inhibitions about this have crumbled. Plus, he might consider it flat-out inappropriate for a boss to explicitly talk about his sexuality to an employee.
posted by John Cohen at 7:33 AM on October 23, 2010 [1 favorite]

Oy, the torture!

This is a great example of why not to not ask people out via digital means.

Practice saying this: "Would you go out on a date with me?" With whatever preamble or postscript you feel is appropriate.

There is no other way to get clarity in this world than to ask for what you want.

I'm a fan of the British method endorsed above, but find that in American in practice it leads to confusion and missed signals. Clarity is the only way to get clarity.

If you want to wait until this work project is over, so be it.
posted by RJ Reynolds at 8:32 AM on October 23, 2010

Yeah, it sounds like the guy is just being a friendly coworker and he's not looking to develop the relationship beyond that. It's worth considering that maybe he receives emails about PMs and stuff posted to his wall, so maybe he doesn't need to log into Facebook to read them.

Some guys get uncomfortable when a woman they (for whatever reason) are not interested in dating seems to be interested in dating them, and they don't really know how to frankly let her know that they aren't interested and/or available without worrying about hurting her. So they just ignore their advances and hope she gets the hint. Women can be the same way with guys they aren't interested in, of course. To me, it seems like that's what he's doing.
posted by wondermouse at 8:55 AM on October 23, 2010 [2 favorites]

something else to keep in mind, and I say this as someone who also works at a bookstore, is that business really starts to pick up this time of year and the simplest explanation of what is going on may be that he's a lot busier now than he was over the summer. if this is the case, then you have January to look forward to. there will be all the time in the world for flirting then.
posted by spindle at 9:04 AM on October 23, 2010 [1 favorite]

You're not in high-school anymore.You are in the adult workplace, and he's your supervisor. A relationship is inappropriate.
posted by PareidoliaticBoy at 9:33 AM on October 23, 2010

Why not just tell him you would like to ask him out at the end of the project?
posted by KokuRyu at 10:18 AM on October 23, 2010

What KokuRyu said. Just wait until the end of the project, or the end of the 12 months (which ever you can stand to wait for the most). Then, take leave of your job and -then- ask him out. Or he may be waiting for such an opportunity to ask you out instead. However, you do need to chill out just a little about this.....it certainly does sound as if this could be "just friends" on his part and/or that he doesn't want to cross the employer-employee relationship line.

Also, since you describe him as "reserved yet friendly geeky nature" he could also be shy.
posted by DisreputableDog at 11:54 AM on October 23, 2010

she's a volunteer. This isn't a "workplace." She is not an employee.
posted by Ironmouth at 1:20 PM on October 23, 2010

she's a volunteer. This isn't a "workplace." She is not an employee.

I don't see why these semantics are relevant. It is a workplace and she is a worker. She can put this on her resume, he could provide a reference as her supervisor/boss, etc.
posted by John Cohen at 2:02 PM on October 23, 2010

Regardless of whether or not he does like you--and I can't tell really, I'd guess he might mildly like you but not be THAT into you in the way that you are to him--it is kind of a "workplace" situation here and he's probably treating it accordingly. My volunteer job has a sexual harassment policy, hers probably does too, and as long as she's "under" him he may specifically need to keep it non-date-y here.

I think that as long as you are working together, it needs to stay non-date-y. Ask him out after your project's done, but only if you're willing to leave the volunteer job if necessary (same as a regular job) if it gets awkward, or if he says no and you're too embarrassed to stick around, or whatever. He might be interested or not, but either way you've still got this supervisor/employee dynamic going on and he, at least, probably needs to respect that.

Oh, and speaking of Facebook, count me as another person who's super sick of it and hasn't logged in in six months. Not everybody cares about it, so don't use that as a crush-monitor.
posted by jenfullmoon at 3:23 PM on October 23, 2010

Response by poster: Thanks, AskMe, for all your great (and honest) answers. Yeah, this is kind of a messy situation I've let myself get into. It doesn't help that there's a new female clerk at the store who may or may not be interested in him as well. I guess all I can do is focus on the project, try to limit my fantasizing about him, and perhaps ask him out on my last day.

As Winnie-the-Pooh would say: Bother.
posted by tamagogirl at 6:00 PM on October 23, 2010

new female clerk at the store who may or may not be interested in him as well.

So, do you see the problem now, and why any workplace romantic relationship is a really really really really bad idea? Never get involved with someone at work, ever.
posted by PareidoliaticBoy at 6:19 PM on October 24, 2010

Response by poster: Well, after many months of longing and awkwardness, I finally bit the bullet three days ago and emailed him, confessing I had a "bit of a crush on him, and think it's best if I distance myself from the project for a little while."

He never wrote back. Not one word. Not even to say he's flattered, or he understands, or he's "sorry but". My inbox is empty. So not only is he not interested, he's also acting like a coward and a jerk.
posted by tamagogirl at 12:29 PM on January 7, 2011

He's being a coward and a jerk for trying to mitigate the awkwardness of the sitatuation?
posted by phrontist at 5:06 PM on January 7, 2011 [1 favorite]

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