Saw a guy at work on OkCupid, he seems cool--should I ask him out?

July 29, 2011 1:04 PM

This is kind of a follow-up to this question about seeing people on OkCupid that one knows offline in some capacity. I have a similar situation but an added wrinkle: I work with my potential match. Is this a good idea to pursue him or not?

The advice in the question linked above about potentially using information from someone's OkCupid profile to help make things offline happen was quite helpful. I think we've all agreed that it's a better idea to contact that person online initially instead of offline. So that was good to know. My situation is really quite similar, but I work with the guy who's profile I've seen. I've never considered dating a coworker before, but he seems like he'd be a good match, and now I'm stuck.

Some background information: we're both in our 30s, we work at a large company together (~400 people) and in different departments. I rarely see him at work except for in passing in the lunchroom maybe once a week. I do, however, see him at least a few times a week while we are commuting by train. We don't really talk, as I don't know him that well, but we have been involved in the same conversations including other people, and he seems nice. We're not work buddies, but if I saw him in the hallway, we'd definitely say hello.

A few weeks ago I ventured back onto OkCupid and stumbled across his profile. I didn't look at it with my own profile--I have a blank dummy profile for anonymous browsing that I used to look at it because I didn't want to make things uncomfortable. I saw that he's a good match with my regular profile and he sounds like an interesting guy (and I've always thought he was cute). Basically, if I didn't already know him, I probably would have sent him a message. But I didn't, because I don't want things at work to get awkward. However, I've now developed a crush on him and it's kind of embarrassing because I shake and blush a lot when he's around, which I never did before. It's getting time to either pull the trigger or move on already.

I have no idea if he's interested in me. There aren't a lot of single people under 40 at our company, so one of my fears is that if I ask him out, rumors and/or awkwardness will ensue in our small group (some of whom hang out together outside of work sometimes--I have not been invited to any of these get-togethers, not for any malicious reason but likely because I don't work in their department).

So, asking him out via OkCupid--good idea or bad idea? If I do this, what do I need to keep in mind? Any other advice about maybe dating a coworker when our work experience is akin to going to high school together? It's not a perfect analogy (nowhere near as vicious as high school, but there is a rumor mill and we run in different cliques), but I seriously haven't had a crush like this in years. Help...

Anonymous because of work issues and potential weirdness.

posted by anonymous to human relations (16 answers total)

Are you just asking people to vote on this?

I vote yes. Little to lose, plenty to gain.
posted by modernnomad at 1:12 PM on July 29, 2011

"Hey, I know you! We work together at Company X, I'm in accounting. Want to get together for lunch? We can compare okcupid stories!"
posted by headnsouth at 1:14 PM on July 29, 2011 [18 favorites]

I was in a similar situation. Last summer I was browsing OKCupid and noticed the profile of a very attractive guy with a personality that seemed compatible. But I prefer to let guys message me first so I didn't write him. Since I live in a small town, we had a lot in common and he checked his profile pretty frequently I assumed he would message me if he was interested. He never did. Then a couple of weeks later I actually met him in person through some mutual friends.

It was weird because I knew we both had most likely seen each other's profiles but neither of us mentioned it. Anyway, we got along very well in person, I started crushing on him a bit and shortly after meeting he came onto me at a party and we hooked up. He asked me on a few dates and things started out really well but he suddenly lost interest, told me he wasn't looking for a relationship, and this thing dragged out into a long, tortuous drama fest for me because I was really into him.

My advice is NOT to message him because I think if you get to know him in person and he's interested he will ask you out. You can probably assume he's seen your profile and he knows you are single, so nothing is stopping him if he gets the opportunity.

I think you will make things needlessly awkward for yourself if you message him and he turns you down.
posted by timsneezed at 1:20 PM on July 29, 2011 [2 favorites]

flirt with the guy at work
posted by Ironmouth at 1:24 PM on July 29, 2011 [3 favorites]

I had the same thing happen to me on Match.com. I had a mutual match whom I worked with. Funny thing, though: on Match.com (on "paper") she seemed like a great person. But the version of her I knew in real life for quite some time--no way in heck. It freaked me out knowing that she saw me on Match.com at some point, too, as we were a "mutual match," but she never said anything, and I kept my distance for a few months.

My whole point? Your mileage may vary, and I don't think knowing her in person AND on OKcupid really has anything to do with one or the other.
posted by TinWhistle at 1:36 PM on July 29, 2011

I'm with headnsouth. A casual get-together where everything is up front is, IMO, better than a situation like timsneezed's where you have to pretend like you didn't see his profile.
posted by pupstocks at 1:39 PM on July 29, 2011

I had an acquaintance from work contact me back when I was using Okcupid. It was actually really creepy; he sent me a message on the site saying something like "Hey I didn't know you were single, you should have told me if you needed a date." And never actually spoke with me about it in person. Dude, if you were interested, you should have had the guts to ask me out in person instead of sending me a lame message on a dating site. Hell, you should have had the guts to at least have a single conversation with me.

I actually think you really should just bring it up lightly and casually, and I'd personally vote in person- "hey funny thing okcupid matched me with you." Or "hey i saw your profile, what do you think of Okcupid?" That way you're opening up the conversation without forcing the issue; if it goes well, you can always ask him out then. If it doesn't go well or he's skittish, at least it's all out on the table and nobody's hiding anything. Yes, you saw his profile; no, you're not ashamed of that; no, you're not going to pretend you didn't or expect him to pretend he hasn't seen you there.

If you must send a message online first, headnsouth's is a good way to do it-- acknowledge that you know the guy, keep it super light, no pretending, and see where it goes.
posted by nat at 1:52 PM on July 29, 2011 [3 favorites]

I agree with headnsouth, except I wouldn't put him on the spot and immediately ask him to lunch. What if he's not interested in you? He's either going to have to dread going to lunch because he's afraid to lead you on but doesn't know how to say no, or he'll have to say no and then it's awkward for you two if you see each other. It's really a terrible feeling having to turn down someone online who you kind of know in real life through friends. Don't put him in that spot.

But definitely say hi on okcupid, something like "Hey it's Anonymous from work. Fancy seeing you on here! Hope you're having better luck on this site than I am. Feel free to say hi on the train sometime, I wouldn't mind a commute buddy. And don't worry I won't tell anyone at work that you're on here, if you don't tell on me =P" This way you broke the ice, he knows he can say hi and start a conversation if he sees you, and he will do that, if he is interested. If he is not interested, he will continue with the casual hellos without taking it any further, but also without having had to turn you down. And then you'll know whether to get over this crush or not. But hopefully good things will come out of this. Good luck!
posted by never.was.and.never.will.be. at 1:54 PM on July 29, 2011 [4 favorites]

I say ask him out. I think you would regret it more if you didn't do it, than if you did it and he said no (not saying he would say no, of course). You would always wonder "what if".

If you decide to ask him out, do it how ever you're most comfortable. As for the rumor mill, ignore it. I know its hard, but you're living life for you, not them. I know people will always gossip, but at this stage in life (I'm in my 30s also) it just seems ridiculous, particularly in a professional environment.

And, just be prepared for any emotional fallout if he says no or it doesn't work out. It might be painful or awkward at work afterwards, but the risk is worth the potential payoff. Good luck!
posted by Desert Paintbrush at 1:56 PM on July 29, 2011

I'm not so sure about mentioning having seen him on OKcupid in person. I think I would feel creeped out and put on the spot.

That same summer another guy approached me in a cafe and asked me if I had a profile up on a dating site. He was cute and I might have been interested but I was flustered and a bit embarrassed so reflexively I told him I didn't.

I really think you should just flirt with him in person.
posted by timsneezed at 2:03 PM on July 29, 2011

I have run into this situation with people i know and just did a haha, lulzy, wink on okcupid just to let them know that i saw them there... I actually ended up hooking up with one of the girls I did that too because of it, we had known each other for a while but I didn't know she was single and looking until i saw her on okcupid..

I guess it depends on your personality and hell well you know the person. I already know the girl I hooked up with fairly well before i winked at her on okcupid..

Maybe just send a wink or a short messages saying: "Hey, I know you!"

Or, you could always leave him an award or something, since you know him personally :)...

not everything on okcupid needs to be super serious.
posted by empath at 3:05 PM on July 29, 2011

Anonymous because of work issues and potential weirdness.

Work issues and potential weirdness is why you shouldn't try to date this person.
posted by davejay at 3:14 PM on July 29, 2011 [1 favorite]

You don't work together THAT closely and are in different departments. I think it would be easy to get over it quickly if it doesn't turn out beautifully.

Is your profile public? If you want to be cautious you could wait and see if he checks you out first.

If you want to move forward more quickly - I vote for making a move with headnsouth's kind of direct message.

never.was.and.never.will.be.'s script sounds like you are embarrassed about online dating and you're not interested (so many people now meet online it is no longer considered embarrassing as far as I know).

empath's script sounds too vague to me. I just think it's really easy to think someone was just checking in to say hi with something ambiguous.
posted by rainydayfilms at 4:17 PM on July 29, 2011

i think that most guys would interpret any contact via ok cupid at all to be an invitation to flirt, and the more he was interested in her, the more likely he would be to pick it up and run with it. but if he doesn't, an ambiguous 'hey there'... is a bit less likely to cause awkwardness in the office
posted by empath at 5:07 PM on July 29, 2011

What's with all the worry about mentioning that you saw him on OKCupid? I think that's a non-issue. Talk to him in person, flirt with him if it feels right, ask him out to lunch, and take it from there. Don't worry about whether you need to mention the profile. You don't.

Whether you need to worry about being turned down or the rumor mill is entirely up to your personal tolerance for mild -- or what I would call -- mild embarrassment. Think about what, in five or ten years, you think you would regret more: being the object of some gossip or not trying to make a connection with someone you seem to like.
posted by Philemon at 6:49 PM on July 29, 2011

I think it's fair game. He works in a different department, so it might be difficult to get to know him in real life. I say, ask him out on Okcupid. I, too, like Headnsouth's message blueprint.

So what if nothing comes of it? At least you'd have nothing to regret, and who knows? Your invitation might be welcome :)
posted by skybluesky at 9:37 PM on July 29, 2011