How can I convince distant co-worker her to take a leap of faith on me?
May 13, 2007 9:58 PM   Subscribe

I normally don’t date co-workers. But I've recently became smitten with a distant co-worker. We've become great friends in the past month and I asked her out tonight. ... but I received a mixed response. (See full post for the whole background) What should I read into her reaction? How can I convince her to take a leap of faith and just try it out? And/or what should I do next, if anything?

I normally don’t date co-workers.

But recently, I’ve become very friendly with a female working at my job. We’d been distant friends through friends for about a year and recently over the last month have been hanging out more and more. We now talk almost daily. Joke around. Go out (in groups and sometimes solo) and have a great time. And I thought we were really connecting. I’m smitten with her.

So tonight I asked her out… Like out on a formal date.

At first she cracked a big smile and said yes. Then paused and said she was concerned about the dating work people thing … and then there was a long awkward pause and smiles… so I said, “Well, no pressure, think about it and we’ll talk.” We smiled and she agreed to that and leaves for the night.

20 minutes later, she calls me and everything’s great and jovial on the phone. She tells me how she digs me, my worldview, hanging out, my friendship, etc.. “This is awesome,” I’m thinking. Then she says she doesn’t want things to go bad at work, so we shouldn’t date. She said she didn’t want to give me the b.s. ‘lets be friends’ line… because she likes me and wants to get to know me better, but she wasn’t sure what to do. The only thing she was sure about was that she didn’t want things to progress and then end and get awkward at work.

We work in totally different departments. We report to different bosses in different sections of building. Our paychecks are printed in the same building and in my few years working here, I’ve only worked on a project that she was involved with 3 times.

I know it’s generally not a good thing to date co-workers but I think we have distance that could fix a lot of the problems that occur when co-workers in cubicles next to each other date.

I have known many people that have worked this out responsibly by acknowledging the work-relationship hurdle. In fact, in the business I’m in (journalism) MOST of the people (including the leaders of our paper) are married to others in the organization or at competing organizations. It’s weird. Journalists tend to only be able to date other journalists (because of the horrible hours/personal values/job demands/etc.).

What should I read into her reaction? How can I convince her to take a leap of faith and just try it out? And/or what should I do next, if anything?

Part of me says, “It sounds like she’d like to try, but you’ve got to fight for her.” She’s kinda cynical and I love her for that. So I think she’s just shutting it down before things have a chance. I know she wants a bold, assertive guy. And I’m normally the kind of guy that’s close friends/crushes on a girl for a while until it develops into a relationship. (My last two relationships were like that.) This time was different, because we connected so well and so fast … I told myself to just step up and lay it out there. And here we are.

Another part of me says this is just an easy way out for her to say no (instead of her saying I’m too old/young/ugly/stupid/whatever).

Any help/anecdotes/advice on what to do or how to date someone you work with are greatly appreciated!
posted by jkl345 to Society & Culture (41 answers total) 2 users marked this as a favorite
Ugh. ... Sorry. The headline should read: How can I convince a distant co-worker to take a leap of faith on me?
posted by jkl345 at 9:59 PM on May 13, 2007

You don't have to convince her of anything, nor do you have to fight for her. She's into you, doesn't know how to handle it yet, but is leaving things open. It's called "taking it slow" and she seems to be taking the lead, so I'd say cool your jets a little and see how things go.

Not everybody solves internal conflicts merely by acknowledging hurdles. You ask what you should read into her reaction, and I say "nothing." Take it at face value because it sounds promising.

Unless you really just want to get into her pants. Rush it all you like if that's the case.
posted by rhizome at 10:05 PM on May 13, 2007

Leave her alone - if she's into you, it will be very apparent. It sounds like you're making her feel uncomfortable, and she can't just say 'no' directly, because she works with you.
posted by four panels at 10:11 PM on May 13, 2007

Part of me says, “It sounds like she’d like to try, but you’ve got to fight for her.”

That part of you is wrong. She said no. The fact that she might under some other circumstances be interested is academic. And if you push it now, she'll change her mind and decide you're annoying and socially inept, and then it really will never happen.

There are some girls out there who, when you ask them out, will say yes, and then go out with you, and eventually have sex with you and become your girlfriend, all without this kind of thing being involved. Go out with one of them instead.
posted by bingo at 10:21 PM on May 13, 2007 [1 favorite]

Yeah, I know you like her a lot, and it sounds like she maybe likes you a lot, too, but it also sounds like she doesn't want to jeopardize her job here.

If you think she needs pushing (as you stated), then can you propose that you go on one "off-the-record" date, and if it turns out horribly, never mention it again to anyone, especially at work? And if it goes smashingly well, then go slowly from there?

If she says no to that, then I'd stop and drop the subject entirely. If she says no, then she probably is looking for an easy way to say no without hurting your feelings too much. Without knowing her personally, she could be somewhat interested in dating you...OR really interested in being awesome work buddies who click well on a platonic level. So respect her wishes if it happens to be the latter; keep in mind that she said no, already though. So don't push it too far.
posted by universal_qlc at 10:33 PM on May 13, 2007

This happened to me on Friday. Without going into identifying detail, I had a series of increasingly interesting conversations over the phone and E-mail with a woman who is dealing with a project I am running.

When the project suddenly began to end, her tone became more flirtatious. Then I brought up having a drink. At first she was like yes, then maybe.

I just kept flirting. She kept flirting back and then suddenly decided it would be "OK" if we had a drink.

Just keep it up the way you are going.
posted by Ironmouth at 10:36 PM on May 13, 2007 [2 favorites]

Also another woman in another project kept flirting with me and I eventually caved in despite my concerns. That drink is Tuesday. Just make sure you aren't breaking any rules.
posted by Ironmouth at 10:37 PM on May 13, 2007

I'm married to an ex-coworker in what appears to be a very similar situation to you (worked in the same office, but in different departments in different parts of the building and our jobs rarely coincided), so I feel like I have some knowledge in this area.

I hate to be downer, but my gut tells me the work situation is just a convenient excuse for her to say "No". No long-term relationship begins (or should begin) with one party wearing down the other by coming up with a compelling argument to counter the initial "Nay".
posted by The Gooch at 11:22 PM on May 13, 2007 [1 favorite]

"If you think she needs pushing (as you stated), then can you propose that you go on one "off-the-record" date, and if it turns out horribly, never mention it again to anyone, especially at work? And if it goes smashingly well, then go slowly from there?"

This is a good answer, one I wish I'd thought of myself. Aside from that, just be cool, man. You know, make sure that she knows that you're still interested, but don't go out of your way to bring up being still interested, y'know? Ball's in her court. Good on ya. Now you just gotta abide.
posted by klangklangston at 11:39 PM on May 13, 2007

Whoa, thanks for all the responses so far! I think I'm over thinking things and appreciate the advice here. I can't believe I said "fight for her" ... wtf is this robin hood? Jeez.

Fyi, all: (I didn't make this clear) but she and I are in no danger of losing our jobs if we date/get married/etc. If we get in huge blow out argument on the job, we would get in some trouble (just as we would if we were friends) but there's no policy against dating coworkers and as I said, we're not co-workers in the same department. So we don't really affect each other's work or interact on the job often at all.

Gooch - Thanks for the honesty. :) (that should be an awkward smile) I do know a handful of folks that are happily married, when initially one or both parties didn't like the other. It just takes some "wooing" and chemistry to develop. But I do agree, it's not the best way to start things off.
posted by jkl345 at 11:44 PM on May 13, 2007

Well, The Gooch is right to an extent. You shouldn't need to convince her, but if you keep up the level of flirtation or take it up a notch, she will be forced to make a decision.

I don't feel that you ought to do this, however because there is too much at risk and it isn't like you can just walk away from the situation as if you had been in a bar.

The best bet is just continue to be who you are and if you are really in it for the long haul... maybe it will work. Just focus on her cues, and keep being awesome. She'll let you know, one way or another. Did I say keep being awesome? Go out with your friends and tell her about the fun that are having in your life. Maybe she will want to be a part of it after all.
posted by |n$eCur3 at 11:44 PM on May 13, 2007

Just keep it up. Be friendly respectful professional but let her know that you have serious feelings about her and that as and when she's ready, you'd like to date her.
posted by londongeezer at 11:59 PM on May 13, 2007

if a girl is really into you and you ask her out, she will say yes. period.

she's using the work situation as an excuse to say no without outright saying no. i suspect that this is because she enjoys you as a person—and it seems that she does want to get to know you better—but she has no romantic inclinations otherwise. and flirting is no indication of whether a girl likes you or not. there is flirting because it makes ppl feel good and flirting with intention. i'm naturally, even unconsciously, flirtatious and i flirt with everyone, male and female—and it has no bearing as to whether i want to date them or not. i do it because it makes everyone involved feel good about themselves and i am all for that.

this is not to say she won't ever see you as a potential romantic interest—she very well could once she gets to know you better—but for now, she's not into you. so don't push it and don't do whatever you think "fighting for her" involves. unless she is some weird game-player that needs a guy to prove how much he likes her (which, you don't want to be with that girl anyway) that will just make things awkward for her and she may then not want to hang out with you anymore at all and that would probably suck for you.
posted by violetk at 12:15 AM on May 14, 2007 [1 favorite]

To the poster and all the people who are saying, "She's saying 'no' and trying to let you down easy" ... I'm not so convinced. Because:

So tonight I asked her out… Like out on a formal date. At first she cracked a big smile and said yes.

I don't think the girl in question would've ever said a flat yes to a date if her end goal was to gracefully extract herself from the situation.
posted by WCityMike at 2:24 AM on May 14, 2007 [1 favorite]

Don't shit where you eat ;-)
posted by chuckdarwin at 4:00 AM on May 14, 2007

What londongeezer said. You're trying to date her, not sell her life insurance. Actively convincing her to do something she's not sure of is not really the best idea in this context. Just enjoy the flirtation, and eventually she'll decide it's worth the risk and take you up on your offer, or things will cool off on their own (and you'll have avoided a potentially messy coworker breakup).
posted by AV at 4:56 AM on May 14, 2007

When you asked her out, I think she heard a friend-to-friend invitation, rather than the "formal date" you had in mind. It's quite possible for her to like you but not want to get involved romantically with you. Heck, she could be gay! You've got a crush on her. Back off and treat your co-worker with respect.
posted by Carol Anne at 5:39 AM on May 14, 2007

I think you messed up when you said:

“Well, no pressure, think about it and we’ll talk.”

Letting her think herself out of it isn't going to help you.

You are probably better off continuing to meet her for casual dates and talking to her. Ease her fears but don't plan out the future with talk of "when this gets into a deep relationship then we can deal with it", etc. It may help to convince her that you are both adults and you can be discreet if need be.

But at this point just continue to be flirtatious, casual, and friendly. You can never convince her to go out with you by arguing the point. The best way to convince her IMHO is a good kiss.
posted by JJ86 at 5:43 AM on May 14, 2007 [1 favorite]

if a girl is really into you and you ask her out, she will say yes. period.

True. But three times in my life I've gotten to be friends with a girl, asked her out, been turned down, stayed friends with her, and between .5 and 6 years later she asked me out. My experience seems to be abnormal, but I'd say just continue to be a nice guy and good friend and don't expect anything. The best way to be attractive to someone is to be happy with what you have. If she really is interested, something will happen eventually.
posted by dfan at 5:45 AM on May 14, 2007

Jeez, Ironmouth, where are you working? I think I need a new job. :)
posted by ClaudiaCenter at 8:22 AM on May 14, 2007 [1 favorite]

To the poster and all the people who are saying, "She's saying 'no' and trying to let you down easy" ... I'm not so convinced. Because:

So tonight I asked her out… Like out on a formal date. At first she cracked a big smile and said yes.

I don't think the girl in question would've ever said a flat yes to a date if her end goal was to gracefully extract herself from the situation.

Maybe. But the problem is, you're just going on a hunch. You have absolutely no way of knowing that is/was going through this woman's head. To counter your theory, it's also entirely possible that she said yes because she was put on the spot unexpectedly and isn't good at saying "No". So after committing herself to something she really wasn't interested in, she took some time to think up a surefire excuse to get out of if (the "I don't think I should date someone I work with" line).

Maybe this theory is wrong too. We have no way of knowing. So all we can do is go on what this woman *actually* said, which is *No*. To continue to try to woo her may be fine if these two didn't work together, however I think people are steering the OP in the wrong, and possibly a dangerous, direction by telling him to keep pushing. In a work environment, that's called harassment. The woman knows the OP likes her. The ball is in her court now.
posted by The Gooch at 8:54 AM on May 14, 2007

If she says no, she means no. That's pretty simple. To continue badgering her after she has said NO means you are harrassing her, possibly even stalking her.

You don't want to be a stalker, do you?

Please try to look at this from her point of view. Some guy she works with wants a date, and won't shut up about it. He won't take the hint that she is not interested. And yet, here he comes again! She's tried to be nice about it, tried to make it not about him, tried not to make an enemy of him because they have to work together and they have mutual friends. But the fact of the matter is that she doesn't want to date him and yet he won't stop asking.

BTW, making up excuses for why a woman who says no really means yes ("she's confused", "she doesn't want to make problems at work", "she just doesn't know she loves me yet") is pretty much page two of the stalker handbook.

Let go, she said no.
posted by ilsa at 9:50 AM on May 14, 2007

I asked my boss out after a few months of crushing and what seemed like a mutual flirtation. He said yes, and then immediately qualified that it wasn't a date, because he couldn't date an employee. So we went out to dinner "as friends" and it was immediately apparent that we were a great match. After our second non-date, he told me all the reasons we shouldn't get involved...and then he kissed me goodnight, and we never looked back. We've been married 8 years.
posted by Biblio at 10:25 AM on May 14, 2007

The best way to convince her IMHO is a good kiss.

uh…seriously? is this a joke? if a guy asked me out and i said no and then he tried to kiss me, i'd a) contact HR about harrassment, and b) probably avoid that guy like the plague. because that's creepy. and completely inappropriate.

guys, get a clue. when a girl says she doesn't want to go out with you—for whatever reason, whether you think she means it or not—leave it. if she did want to go out with you sometime down the road, she knows you're interested, but until then don't keep trying to "convince" her. why would you want to date someone who needed convincing to go out with you anyway?

I don't think the girl in question would've ever said a flat yes to a date if her end goal was to gracefully extract herself from the situation.

no true. a lot of ppl will will agree to things when they are put on the spot, especially if it's in regard to something unexpected; almost like an automatic response. what matters in this situation is that she called back and declined—after giving the matter some thought.

you are just proving my point. the girls turned you down initially, knew you were interested, and awhile down the road after they got to know you, asked you out. if they were really into you when you initially asked them out, they would have said yes. period. i mean, if i had a crush on someone and he asked me out, i'd be so stoked! i'd say yes, and then call my girl friends to tell them hotstuff mchotterson in building B just asked me out. i would never turn down a date with someone i was interested in. cause that's just stupid.

your situation is different: your boss agreed to go out with you. this girl said no, not "yes, but we can't call it a date." not sure how your story is relevant except to encourage someone to press a suit that he shouldn't.
posted by violetk at 11:30 AM on May 14, 2007

violetk said: if a guy asked me out and i said no and then he tried to kiss me, i'd a) contact HR about harrassment, and b) probably avoid that guy like the plague. because that's creepy. and completely inappropriate.

If I understand this thread correctly we aren't talking about you, we are talking about jkl345 and his coworker who he already has a strong friendship with. Different story than where you want to take it.

My advice (try quoting so we know who you are talking to) wasn't for any random person in dealing with a coworker they like. I am also not saying he should go up to her at work and plant a big kiss on her lips. If the time is right and the signals are right, the best way to tell if you are both on the right page is a kiss and I stand by that advice. If she pushes him away or evades him at that attempt then the message is pretty clear. Much more clear than a yes/maybe/no/call me later.
posted by JJ86 at 1:44 PM on May 14, 2007

Both Ilsa and Violetk— While I understand the prohibition against pressing affection where it's not wanted, the thought that this guy's getting mixed signals and still wants to date the girl makes him a stalker, or means that he's sexually harassing her is such amazingly blinkered and simplistic advice that it does him less than no good.

The only thing he needs to know is that he can relax and let her make the next move, while continuing to show interest. As for anything else, it's presumptuous to attempt to force his scenario into your anecdotal weirdness.
And yeah, some of us have gone on dates with girls who first told us no for some reason or another. I went out with a girl I used to work with once she quit for a couple months. She didn't want to date me while we worked together, and I respected that. But the thought that she's immediately scanning the room for fire exits is pure paranoiac fantasia.
posted by klangklangston at 1:45 PM on May 14, 2007

JJ86 and klangklangston:

she said no. end of story.
posted by violetk at 1:56 PM on May 14, 2007

and JJ86:
if she had told the guy that she doesn't want to go on a date—because that implies a romantic inclination—for him to then kiss her when they are out is still really inappropriate. she had already made it clear that she wasn't interested in a romantic relationship with him when she said no. she knows he's interested so if she does change her mind, there are a number of ways she can communicate that but she doesn't need to be pressed about it by him thinking he should kiss her as a way to change her mind.


i never said that she—or anyone—would be "scanning the room for fire exits" because of being asked out once. i said that if the guy keeps pushing to go out or trying to convince her they should or kisses her when she had already declined the date, then it is likely to make her very uncomfortable to be around him.

and it's interesting that there aren't really any responses on here from women telling him to go ahead and try to push the situation, much less try something like kissing her. or that the two responses who are saying that i or ilsa or anyone else who would find it inappropriate to push things both come from men.

posted by violetk at 2:07 PM on May 14, 2007

That's both totally mischaracterizing what I said and what the OP said, which leads me to believe that you're not at all a reliable judge of this situation.
You want any more outta me, take me to MeTa.
posted by klangklangston at 2:10 PM on May 14, 2007

klangklangston, wow, now attacking whether i am able to "judge" the situation?

i thought ppl come here to ask opinions of other ppl. i gave an opinion based on what i read and what my experiences are as a woman and how i think women (based on my lifetime experience talking with my girl friends about our experiences in dating and social situations) may react to the given situation.

defensive much?
posted by violetk at 2:17 PM on May 14, 2007

violetk said: she said no. end of story.

What thread are you reading? Please re-read. Nowhere did the OP say that the girl said "NO". She said "Yes" and then later said she was "Unsure".
posted by JJ86 at 2:18 PM on May 14, 2007


sheez. guys, come on. i mean, maybe you guys don't want to believe this, but if she wanted to go out with him, if she was interested in him romantically, if she wanted to date him, she would have said yes and that would have been the end of it. no guessing, no nothing.

she called back because she wasn't interested in going on a date with him. who cares what her reason is? she changed her mind. i'm just saying, if a girl digs you, she isn't gonna say yes and then back out of it. how is that so hard to understand?

i didn't tell the OP to never talk to her or hang out with her again. i just told him to let that one drop and if she changes her mind, she knows he's interested and can proceed from there. otherwise, most girls i know would start feeling uncomfortable if the guy keeps bringing it up.
posted by violetk at 2:28 PM on May 14, 2007

p.s.: "unsure" ≠ "i'm just being coy about this, and if you keep on keeping on, i'll eventually say yes and mean it."

i don't know about anyone else, but it seems to me that if someone really wants to do something, they would just do it. they wouldn't come up with a bunch of excuses as to why they couldn't. unless they are really into self-denial. or unless they don't want to do it.
posted by violetk at 2:40 PM on May 14, 2007

Jeez, this really broke into a dogfight.

Thanks everyone for feedback. Especially those that realized I'm not a stalker/trying to pin her against the broom closet and make out with her.

She contacted a close friend of mine about the situation, and said she'd like to try it but is apprehensive about the coworker thing because of a friend of hers who had two really, really bad office relationships. Like so bad, I didn't even work here when they went down, but I still hear legends about the arguments and drama.

Obviously, she and I are not in a similar relationship as those two previous train wrecks and we're in totally different wings of the building/departments so there's some distance. (The two train wrecks were within cubicles of each other so it was hyper-pressurized). So it's basically freaked her out about office romance. So maybe it wasn't an excuse after all (yay!).

So we talked briefly and we're going to have coffee this week and talk more about things. Take it slow. See where things go.

Thanks again for all your help!
posted by jkl345 at 2:54 PM on May 14, 2007

well, that's awesome to hear!

good luck!
posted by violetk at 3:04 PM on May 14, 2007

So turns out that while "no," might mean end of story, "unsure" doesn't...

Hope everyone here learned something today...
posted by JakeLL at 3:35 PM on May 14, 2007

Oh and good luck jkl345!
posted by JakeLL at 3:36 PM on May 14, 2007

To be clear from above--my situation Friday was resolved when she emailed back and said that an "unscientific poll" of her "multiple personalities" determined that it was OK to have a drink with me. People aren't always of one mind.
posted by Ironmouth at 5:38 PM on May 14, 2007

Claudia Center, I do the exact same thing you do. Exactly.
posted by Ironmouth at 5:40 PM on May 14, 2007

I do the exact same thing you do. Exactly.

sniff! so it is me -- it really really is me ... {jumps out window (though only from second floor apartment)}
posted by ClaudiaCenter at 12:57 AM on May 15, 2007 [1 favorite]

sorry Claudia, what I meant to say was that we have the same job (same area of specialization). Without going into detail, projects means "cases." thus my dilemma.
posted by Ironmouth at 3:37 PM on May 28, 2007

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