Is there ever any appropriate way to hit on a coworker?

So as a preface, let me just say it seems like the “safe” answer is probably no.

But we have a person who started at the company I just started at at the same time as me. She’s cute, interesting, and we ended up working together on an IT problem she had for like… an hour, and got to talking. She’s very friendly, and I’d like to ask her on a date, but I’m not sure if this is appropriate or not, or under what circumstances.

(She’s in a different department, but given that I work in IT, chances are good we’d have something to do with each other eventually. Which seems potentially bad.)

I’m sure you will get a lot of negative answers but I just want to say that I met my husband when we worked together and I was his boss! (Actually there were two of us supervising his department so I let the other boss write his reviews.) We began dating soon after he came to work for the company, and after 34 years we are still together and have been married for maybe 10 years (neither of us can remember what year we married and we can’t find the license, so…). Just letting you know that although there are a lot of reasons it might be a bad idea, it does not have to be.

The answer is obviously yes, since many, many married couples met at work. Do you get to leave your desk for lunch? That’s a much less romantic time than a “date” and you could really get a better idea if this is something she’d want to pursue – grab lunch together, talk about whatever, and get a feel for whether she’s interested. If so, then maybe do that again, or get coffee – if she keeps agreeing to get together to hang, maybe suggest a couple of drinks after work. I would go that way than going right to a “date” – keep it more casual and closer to work oriented at first.

If she continues to show interest, then, sure, see if she wants to go out to dinner or show or whatever you have in mind. If she says no, then back off.

Good point, RitterSport. My husband and I started our relationship by having lunch together several times before having a date. Excellent idea.

I met my wife at work. We dated for 3 years before getting married.

I like RitterSport’s ideas and approach. Why not try that?

ETA: ninja’d by kayT, and we agree!

It is when a person doesn’t accept “No, thank you” that it becomes a problem.

Just remember that you are at your workplace to do your job, so whatever you do, don’t let your romantic feelings get in the way of that. That being said, I think it’s perfectly fine to try to pursue a relationship with someone in the workplace. There are ways (as mentioned above) to do this without coming across as creepy or that are in violation of any sexual harassment policies.

Repeated for effect. If you are not emotionally able to be casual about whether or not she’s interested in going on a date with you, just stay away from it altogether.

Yes, yes there is. But I might suggest just making a friend of her first, and then dialing things up when it feels natural to do so and her reactions are a bit more predictable. And ya, shut it down immediately when there’s a “no”.

She says it all started when I walked by her desk on the way somewhere. She felt my presence and looked up just in time to see me disappear behind a cubicle. She turned to her coworker and said, “Who is THAT!” “Oh, he works over in B wing. Calm down, he’s married.” About a year later she ended up being promoted into my department so we had some interaction in team meetings, but I still never really saw her until one day she just hijacked a trainwreck of a meeting, got it on course, and got everyone to agree to a course of action–so impertinent and so confident! Her email signature was “Save the Earth, it’s the only planet with chocolate!” So every now and then I’d leave a See’s chocolate at her desk (I usually kept a 2# box around for nibbles & sharing). Professional emails between us started to include double entendres that we’d ‘accidentally’ escalate–all very cute and never deteriorating into anything really unsavory. Just blowing off steam. In unrelated events I finally filed my divorce and became free. Same time, she ditched her long-term guy and moved back to her mom’s. My car died, she noticed I’d been walking to work, she started giving me rides to work, we started going to lunch together. I believe that started with her saying something like, “You should take me for lunch.” And so I took her to a restaurant for lunch. Walking up the stairs back to the office she got pouty and said, “That’s not what I meant.” So I planted one on her and, well, our 10th anniversary is in 11 days.

Worked together for an hour and got to talking…not just yet! After a few more neutral type encounters would be more appropriate, I think.

After a single short encounter seems too soon, and likely to get a ‘no’, response. Give it a little more time. If she’s felt at ease around you a few times, you have a better shot, to my mind.

Good Luck!

Yes, if you son’t let it interfer with your work, and if you take NO for an answer the first time.

My story: The store I worked at hired me as a temporary, part-time holiday cashier. After the holidays, I was kept on as a full-time temporary cashier until a spot opened up. A cashier and an aisle worker ended up getting together, and she decided to become an aisle worker. So when an aisle worker quit, she got the spot and I got her cashiering spot.

Be attractive. DON’T be unattractive.

I don’t see a problem unless there is a “boss/subordinate” thing. But then again I’ve been fired more often than the average artillery piece, so my opinion about workplace shit might not count.

Honestly, I think this is maybe the best dating advice there is for straight guys, regardless of whether it’s in the workplace or not.

I’ll be stealing this. I’ve got a young man under my roof I can use it on. Kid can get a job like nobody I know, and get fired within a week. Usually because he can’t be bothered to get out of bed.

I would say that if your relationship is such that you need to actually ask the coworker to go on a date, then no, you shouldn’t do that. It would mean that your relationship is impersonal enough that you’d likely be crossing a line by asking. If she doesn’t want to go on the date, it has the potential to make her feel uncomfortable and create an awkward working environment.

It’s okay to date coworkers, but only if the relationship develops naturally in that direction. That can happen if you work together on a regular basis or see each other often and have lots of opportunity to get to know each other in a platonic basis. Then it should be obvious if you are just friendly coworkers or if there’s something more. You wouldn’t need to ask about going on a date because the relationship would have progressed from work lunches to fun lunches to happy hours to dinners and so on. If either of you didn’t want to make progress in the relationship, it would be easy to show lack of interest and there wouldn’t be misunderstandings.

What’s wrong with “Hey, would you be interested in going to dinner on Friday?”

If she says “No” then just say “Okay, no problem” and don’t bother her again.

If she says “Yes” then it’s all good.

You will presumably be working with her in the future on other projects. If you ask her on a date and she says “no”, what will that mean for those future times you’re working together? Unless you either already know that she’ll say “yes”, or already know that even if she says “no” it won’t be a problem, then you shouldn’t ask her out. If you’re not sure, then you don’t know her and/or the situation well enough yet, and so you shouldn’t ask her out.

The time may come when you do know for sure. But given that you’re asking us, that time has probably not yet come.

Sure, there are many times it works out all right - many happily married couples met as coworkers. There are many times when it backfires, but you just have to be careful. But you have to be extremely careful about reading her signals. It’s very easy to mistake a woman’s casual, public friendliness as the “open-to-something-more-than-just-friends” friendliness. Try to observe her interacting with other male coworkers. Does she treat every single one of them the exact same way she treats you? Then maybe she is not open to a relationship with you. On the other hand, if she is noticeably more friendly or personal with you than others, then maybe there’s something.

My $0.02

While good, lasting romances have started in the workplace (as stated above), woe be to you if you get into a relationship and you break up or get really serious. Sometimes it makes for a really awkward situation in the workplace, because somehow others will know.

That said, I’ve gone out with co-workers, but always kept it a friendship level. Rumors flew, but that didn’t bother either of us because we both knew we were just friends.

As others have said, take it slow and let it progress naturally. See if chance meetings in the hall are more than “How are you?” and if she eats in the lunchroom, arrange to coincidentally be there too.

Also, keep in mind that most people are nice to the IT guy/gal, because you’re doing something for them, and they need your service. I’ve known IT staff who put those who annoy them on the bottom of the ticket list when possible.

A few big Don’ts.

Don’t spend more than a few minutes chatting in the hall or anyway else. You’re both there to work and neither of your managers or co-workers will appreciate your taking time away from work. Remember that every minute you spend together is 2x the work not being done.

Don’t ask her co-workers about her. That’s just creepy and may be considered harassment.

Don’t assume she’s single and ready to mingle. I once almost asked a manager (who would chat me up) out to the movies. Turns out she was the owner’s girlfriend!

Don’t make it obvious, especially to your IT co-workers that you’re really interested in her. IT staff generally know and visit just about everyone in the company and they may inadvertently let it slip that you’re interested and rumors may fly. May not bother you, but it may bother her.