Asking out a workmate: should I do it?

In My Humble Opinion
1

Greetings fellow Dopers,

I’m way inexperienced in these matters, so I turn to the wisdom of the anonymous masses for advice. The premise is going to sound kinda clinical at first, so please bear with me.

I’m a 26-year-old man interested in a 24-year-old woman. We work at the same company and in the same department. We met last year when we were both on the same project team for a few months as developers.

Toward the tail-end of the project, we had a longer conversation than usual and learned that we lived close to each other; her apartment’s just across the street from mine.

Every so often, she invited me to group events, always involving other workmates. Some were casual meetups of a handful of us at restaurants/bars, others were small gatherings at her apartment (3 or 4 people total).

We’re no longer working on the same team, but we still see each other at work every day. She continues to invite me over her place (about once a month) along with other workmates in our department.

We’ve both been single for a while, no roommates. She is distinctly friendly, deadly intelligent, and always fun to talk with. In addition to her natural charisma, she’s also totally attractive, which essentially makes her overall charming from bits to bytes.

I’m very eager to ask her out, or at least meet her without the work gang around. The problem is, I don’t want to make things awkward for her at work if she’s not interested, and I fear she might not be so keen to keep inviting me if she knows I’m lusting after her. Things are great at work, and I’ve always subscribed to the “Don’t rock the boat” mentality.

At the same time, I really do like her (for several months now). It’s also been years since I’ve been on a date, so I’m not sure if it’s the build up of hormones driving my emotions here.

How should I proceed? Is my lack of recent experience clouding my judgment? Is there a casual way to approach this and feel her out? Should I trust my feelings and just go for it? The fact that I’m thinking so critically about it makes me wonder if I’m being silly. Or does that sound crazy?

I’m a normal guy in most respects, but this whole situation is making me think I’m going batty. Please help me out, SDMB!

2

Nothing ventured, nothing gained. The worst thing that could happen right now is she says no.

Do nothing, and you’ll always wonder what could have been.

As far as the dating a co-worker thing, you’re 26. It’s highly unlikely you’re both going to work there forever. But you have to ask her out first (and have her accept) before that’s even an issue, so let’s just go one step at a time.

3

Are you going to be cool if she says no, or are you going to be weird? If you’re going to be weird, skip it. Realize that if she does say no, the dynamic might change. If you’re fine with potentially not getting invited to any more stuff, give it a shot. Ask if she wants to hang out sometime, just the two of you.

4

Same department? I say no. I made that mistake twice and when it ends, it’s torture on everyone. Same company, but far enough away (different floors, building, etc.) is ok, imho. But even then, you should consider potential crossed paths due promotions, transfers, etc., which can potentially affect your career. Imagine if you miss out on a promotion because she’d have to report to you and your manager decides it’s not a good idea?

5

Sounds like she does all the initiating. Take a step and ask her to do something just the two of you. Make it something simple. Don’t overanalyze it. You’re not asking her to marry you. If she says no, don’t make a big deal about it. There are lots of women out there.

6

Take it even slower, invite her out with work mates. See how that goes.

7

Nope it’s gotta be just the two of you. Get her to come out for dinner or coffee. Something where you can be alone and talking. If things are going well invite her back to your place to listen to music/have a glass of wine/etc. You are in friend zone so you gotta make that move if she is giving the right signs or play it cool if it’s obvious she only wants to be friends. You will never get the opportunity to assess the situation if you’re always around 3-4 other people.

8

And when it’s over?

Will you still be comfy with the after-work get-togethers?

What if you’re both assigned to another project together?

Will you make it difficult for your manager - Joe and Karen would be the best pair for this, but there’s that tension…

Unless one of you is ready to move on should it fail, go incredibly slow - as in don’'t go there.

9

Just ask her to go to lunch or coffee or something. If she says she’s not interested, it’s not like you were proposing to her or anything.

10

Thanks for the advice, everyone. It feels good to hear different opinions.

No, I won’t go weird if she says no or if things don’t work out. Despite the panic I might’ve conveyed in my first post, I’m very mellow and calm in person. I’m more worried about her own feelings after the fact.

It sounds like the best thing to do is to ask her to do something casual, just the two of us, and feel out the situation. The advice from Stringbean resonates with me; I can gauge her comfort level and see if she’s open to something more intimate or only interested in friendship. She really enjoys coffee, so it should be pretty natural to suggest it.

If I’m sensing friendship-only signals, I’ll take it easy. I just hope I don’t misread anything or miss an opportunity because I came on too weakly.

But, hey, I’ve gotta try.

11

If you want to ask her on a date, then ask her on a date. Don’t ask her on a ‘thing’ where she’s unsure whether it’s a date or just two friends meeting up. That’s where it will get awkward.

Good luck!

12

um… no. According to my brother’s direct personal experience, the worst thing that could happen is he gets fired. Just sayin’…

13

Explain.

14

If she isn’t interested, there is a better than average chance it will be awkward whatever he does. Maybe awkward enough to impact his job. He can’t control her reaction to finding out he likes her as more than just a friend. It might be “gee, its about time you said something, I’ve been waiting.” Or it may be “oh, gee…um…yeah…thanks?” Followed by her wondering if every time he looks at her he’s imagining her nekkid for as long as they work together. Which seldom makes for a comfortable work relationship.

15

My brother worked with a team in San Francisco that had a Murphy Brown kind of setup, where every Friday night at quitting time, everybody would head down to the corner bar & grille to have a sandwich and a beer before going their separate ways for the weekend.

One Friday, my brother & a female co-worker missed the elevator that everybody else took and, while travelling down in the next elevator, he said something along the lines of “hey, you want to go grab a sandwich & a beer?” meaning, “… along with everybody else in the group…” She said no, and when they got to the ground floor, he headed for the bar & she went the other way.

Monday morning, he’s cleaning out his desk, fired on charges of sexual harassment.

Worst case scenario. Well, no arrest was involved, so maybe next-worst.

16

There is more to the story than that. That’s not how sexual harassment regulations work. They typical requirement is that the action much be repeated, directly sexual and clearly unwanted. Either you are exaggerating or your brother is telling tales.

17

That’s the story as he told it, so I guess my brother’s a big, fat liar then. Thanks for the tip.

18

Is it possible the “more to the story” bit was more aimed at the woman? Maybe she lied about what all had gone on or said that your brother had been repeatedly harassing her?

19

You don’t know - can’t know - the “or if things don’t work out” part.

One thing we do know about most breakups, is that one party wants to break up and usually one party doesn’t. How that “doesn’t” party acts is anyone’s guess. It could be fine, but it could be a mess. You don’t know and she doesn’t either.

Needless to say, the closer you are to her, on a day-to-day basis work wise, increases the risk if things go south (and let’s face it, they usually do).

20

I disagree. She considers him a friend. He needs to wiggle his way out of friend zone. Time between the two of them where they can talk comfortably is the way to negotiate that line. The formal setting of a “date” achieves the opposite. Nerves are high.

OP: Low pressure. Coffee or a drink. Act flirtatious and outgoing. Make her laugh, and subtly sexualize the conversation: “when did you have your first kiss? when was the first time you fell in love? when did you lose your virginity?” Work your way up to that last one.

Do not tell her you like her. Actions will be more effective. If it’s going really well invite her back to your place. If she agrees, give her room for the first few minutes, then make the move.

Even if she doesn’t like you, you may well have charmed her enough to fool around with you.