Another should I ask her out question

August 24, 2016 6:21 PM

There's a woman at work I've been thinking of asking out. I just saw her profile on a dating site. How to ask her out?

Do I ask her out at work? On the dating site, she will see that I visited her soon enough. Could I say hi through the dating site? Would that be creepy?

posted by falsedmitri to Human Relations (14 answers total)

Without knowing more about the woman, you, and your professional relationship- eek! Tread carefully here. If you must pursue this, start by getting to know this person. See if you have common interests, etc. Don't bring up the dating website unless she does. Ask her out for a drink once you've gotten to know each other better. If she declines, accept it and don't ask again.
posted by arnicae at 6:34 PM on August 24, 2016 [10 favorites]

Pretend like the dating profile doesn't exist.

Run into her in the cafeteria and start chatting. If you get any green lights then ask her out.

After like a month of dating you can say "funny story...."
posted by St. Peepsburg at 6:44 PM on August 24, 2016 [16 favorites]

I think running into colleagues on dating websites is an "occupational hazard," especially if you work in a niche field or live in a smallish community. With the usual caveats about dating coworkers, if you want t ask her our on a date, I would do that on/in the venue designed for that: the dating website. Not your workplace.
posted by pinkacademic at 7:16 PM on August 24, 2016 [6 favorites]

Funny, my take on this is different from pinkacademic's. I see dating sites as a way to link up people who wouldn't otherwise know of each other, not as a way of siloing off dating-related activities from the rest of the world. You already know this woman and were thinking of asking her out, so I'd do it the traditional way by asking her in person. I would treat the dating profile as inadmissable evidence, which is to say I'd do my best to forget about it.

All the usual cautions about asking out coworkers apply, naturally. For me though, I would be more weirded out by a coworker asking me out via a dating site versus just asking me to my face. I'd be thinking, "We see each other every day, why are you messaging me on OKCupid as if I were a total stranger?"

Obviously, opinions vary there.
posted by Anticipation Of A New Lover's Arrival, The at 9:13 PM on August 24, 2016 [10 favorites]

With the usual caveats about dating coworkers, if you want t ask her our on a date, I would do that on/in the venue designed for that: the dating website. Not your workplace.

I could not disagree more strongly. Back when I was online dating, I was messaged by an acquaintance. I was very, very weirded out - why wouldn't he just talk to me in real life and see if there was chemistry there? (there was not.)

I have seen many coworkers on various dating websites but none of them ever contacted me, thank god. That would have been so incredibly awkward. And then I'd have to see them every day after that...ugh. Seriously think twice, and then a third time, really hard, before messaging her on the site. Much less potential for awkwardness if you start out casually by chatting etc in real life, then maybe try some mild flirting and watch closely for subtle verbal and non-verbal clues that she's not interested.
posted by randomnity at 12:06 AM on August 25, 2016 [8 favorites]

I went through an experience like this... A trainer at my gym saw me on OK cupid and sent me a message. To be honest iff I had liked him before that I would have sent out signals at the gym. To avoid awkwardness I hung out with him, we went for a jog around the neighbourhood, as friends. Then I ended up quitting the gym because he became really intense!
Get talking to her in real life, and see what signals she sends out, otherwise it could be quite awkward.
posted by akita at 4:01 AM on August 25, 2016

I saw a guy I sort of knew in friendship circles on Tinder. I swiped right and after we matched, messaged him with "Tinder ha? I am telling everyone :)". He proceeded to ask me for a drink. We went on a few dates but it didn't work out (nothing to do with Tinder or my approach).
posted by sockiety at 7:27 AM on August 25, 2016 [1 favorite]

If you've not already felt head-over-heels compelled to ask this woman out face to face, you're not even close to eligible for an exception to the Don't Hook Up With Co-Workers rule.
posted by flabdablet at 7:49 AM on August 25, 2016

When guys I know message me on dating sites it really depends.

The best approach was a guy who I knew through friends and had met indirectly several times, we were friends on social media sites but not "friends", he was just like "how are you finding things on here [funny joke], I couldn't help but say hi", but he wasn't like "hello lafemma, I see you, wanna go on a date?!". He made it so I could ignore the message without awkwardness, which was much appreciated and I still like him irl even though we're not going to date, he understood online etiquette and I felt flattered, not creeped out.

The worst was a guy who I'd been introduced to online for shared interests, and had already turned down indirectly when he started showing interest in me, like "no, sorry not going to that party", etc. He found me on the dating site, made a big deal about how we "knew" each other already, and pretty much forced me to acknowledge him and send a reply (I ignored him on the dating site and he re-sent the messages on facebook so I had to respond), don't do that.

I think due to it being a coworker you should tread carefully. If you are already friendly irl I'd stick to that and ask her out for lunch or coffee, something not totally a "date", and see if she reciprocates your interest. Agreed with flabdablet 100%.
posted by lafemma at 7:54 AM on August 25, 2016 [1 favorite]

The advantage of approaching her via the dating site is that it's easier for her to say no and move on without the issue of negotiating being polite and awkward with someone she'll see every day. The downside is that if you do see her multiple times a week at work, it would be super-weird to get a "message from a stranger" from that person. The advantage of approaching her at work is that it uses a connection you already have, the disadvantage is that it highlights the awkwardness of workplace dating, and would require some privacy (i.e. you don't just stroll up to her open-plan workspace desk and say "Hey Judy, I saw your profile on OK Cupid - great picture!"). I'd say it depends on how well you know her at work, how often you see her, how small and gossipy the workplace is vs large and easy to hide in.

If you do it via the site, definitely acknowledge the situation, and just be honest about your uncertainty. "Judy, hey, it's cool to see you here. I'd already been thinking of talking to you at work about going out for a drink sometime but that seemed so awkward (I mean, imagine if Simon overheard me!). I don't want to weird you out by emailing like a stranger, but I also didn't want to bring it up at work if you totally weren't interested. Would you be free tomorrow afternoon to take a quick coffee break out of the building?"

I say this because you indicated you'd already been thinking of asking her out, and you see the dating site as indication that she's single/looking. If she wasn't on your radar before, then no, the "convenience" of already being acquainted is massively overbalanced by the awful awkward inconvenience of dating a coworker.
posted by aimedwander at 7:59 AM on August 25, 2016

Since you know she's open to dating in general, I don't think that it would completely inappropriate to broach the subject at work. The important thing is to be up front that you recognize that dating coworkers can be/is uncomfortable and give her a very easy out.

So, sooner rather than later, I'd approach her in person, where others are unlikely to hear the conversation, and say something like: "Hey, I know dating co-workers can get weird, but I was wondering if you'd be interested in dinner some time -- my treat."

If she doesn't immediately and enthusiastically say "Yes", be ready to follow up with: "it's cool if you're not interested, I won't bug you about it again"

And then don't bug her about it again, and don't interact with her socially (watercooler talk, etc.) unless she initiates.

This is all, of course, predicated on the idea that you will not be poisoning the work environment if things don't work out. Think about how you will be able to handle it if you go on a date and there's no "spark." Think about how you will be able to handle it if you become a couple and she cheats on you. Think about how you will be able to handle it if you hook up and she gives you an STD. Think about all of the terrible relationship things that can occur, and whether you'd be able to continue to interact professionally with someone who was on the other side of them.

There are people who are horrible human beings in their personal life, but are valuable and professional workers at work. If you can't imagine yourself working on a project underneath someone who put tampered with a condom to get you on the hook for child support, you shouldn't date a coworker.
posted by sparklemotion at 8:37 AM on August 25, 2016 [2 favorites]

Another vote for asking her in person on a date if you think she would say yes (you thought about that right? what would she think? would she find it appropriate or be weirded out? think about it) but either way ignoring her on the dating site.
posted by Potomac Avenue at 1:51 PM on August 25, 2016

Well, definitely *don't* do what someone once did to me (he was a fellow grad student in the same program, whom I had barely spoken with before): "hey nat, you should have let me know if you needed a date rather than going online! I'd take you out anytime".

I probably don't have the wording exactly right, but it somehow served to be a terrible combo of creepy and a poor attempt at a neg. Coupled with the fact that he then avoided me in person for the rest of our grad careers, it a) didn't get him a date and b) was pretty creepy.

On the bright side he didn't end up dating someone at work which is worth avoiding, so maybe a win in the end.
posted by nat at 6:26 PM on August 26, 2016

If it's Tinder you can swipe right and start a light convo on Tinder if you match (she may have only swiped right to be friendly though, so start slow). If it's any other dating site, don't contact her on it and don't mention it- just be slightly more friendly at work and see if there's potential in person.

I'm gonna say right now it's rather more likely she's not into you, because if she was, you have already had lots of time to figure that out- So go slow and back down fast and gracefully if her response is anything less than enthusiastic. Don't be the weird resentful dude at work.
posted by pseudostrabismus at 6:37 AM on October 26, 2016