A perfect storm of complications: acting on a crush on a shy coworker
July 23, 2012 4:36 PM   Subscribe

Despite all advice to the contrary, I'm trying to get to know my shy coworker crush better -- have I made a hash of it? Or does it sound like I'm doing okay?

For several years, I've had a crush on a woman I work closely with. She's quiet and a very private person, with the discipline to back it up in the long term. I've always respected the boundaries she sets with her co-workers in terms of her personal life -- she's a bit of a mystery to most of us.

For most of the time she's worked in our department, I was in a steady, long-term relationship. When the relationship began to fall apart last year -- nothing nasty, just a recognition that we'd been coasting together for too long without any real progress or change -- I made the mistake (I think) of confessing my crush to my coworker. It was a terribly awkward experience, and I felt bad for having foisted it on her out of the blue. Basically, I said, "I think you're great, and it sucks, because I'm with someone, and we work together, and it sucks."(I've paraphrased here; there was a lot more stuttering and near-hyperventilation involved. I'm not particularly smooth or charming in the *best* circumstances, and this was an unmitigated disaster.)

She said... nothing. Or nearly nothing. I figured I had destroyed our working relationship, made a fool of myself, and embarrassed her. I emailed her an apology, and we never spoke of it again.

Flash forward. I've been single for over half a year at this point. I jumped back into dating right away just to prove to myself that I could. Made a couple friends, but nothing ever got serious. And my coworker and I got back on good terms, to where I got the sense that perhaps she actually likes me on a personal level.

A few weeks ago, I worked up the nerve to ask her to go to lunch. This is out of the ordinary -- we both normally eat alone. When you factor in past history, the message I was sending was pretty clear: "I still like you, and would like to get to know you better." We've gone to lunch a couple times since. They were great if not stellar conversations between two introverts. I've learned more about her in two weeks than I had in the previous several years combined. I'm just very worried that I'm misreading the situation, and that she's not interested and perhaps just being a kind person or a good friend.

(And yeah, coworkers. I know. I know. But I've sort of made this choice -- life is way too short, and a question unasked is a regret always.)

At one point, I asked her if she was seeing anyone, to which she replied "No, are you seeing anyone?" I said no, and that I was interested in asking her out, but was not doing it right then and there, mind you. She expressed concern about being coworkers, and joked that maybe after a couple more conversations, I'd find some reason not to like her as much. It seemed promising.

So here's the thing: I asked her out a couple days later, and she turned me down, saying that it was "probably too soon", and that lunch would still be fine. In a subsequent conversation that day, she said in a pretty final way that it'd be "too weird." I got the sense at that point that a door had closed on the whole thing, and wouldn't be re-opened.

But when I asked about lunch later the next day, I found out she's still willing to eat with me next week. So have I been rejected and don't know it yet? Or was I rushing things by asking her out?

It comes down to this: I feel I'm skirting a line between being persistent and being a pest. Quiet types and shy women out there -- have you experienced something similar? What advice would you give to a smitten guy in my situation? Back off? Flag off and save the work relationship? Or something else?

Thanks for *any* insight, encouragement, warning or friendly criticism you can provide. I could use some fresh perspective on this before I sabotage the whole situation by over thinking it.
posted by anonymous to Human Relations (36 answers total) 3 users marked this as a favorite
You've been completely and fully rejected for romantic endeavors. She is still willing to go to lunch with you as friends. Please don't pursue anything romantic with her, though, and if you can't have lunch with her without trying to flirt/ask her out then don't, but it sounds like just because she doesn't want to date you doesn't mean she doesn't want to be friendly.
posted by brainmouse at 4:40 PM on July 23, 2012 [21 favorites]

She wants to have lunch with you but isn't romantically interested in you/sexually interested in you. Or she might be a lesbian and not want to be out to the office. Basically you asked her, she turned you down, listen to what she's saying instead of second guessing her. If she is interested further, she'll need to make the next move.
posted by the young rope-rider at 4:40 PM on July 23, 2012

She knows you want to date her. If she wants to date you (she does not want to date you), she will make it clear in a way that you won't have to make guesses about. But she doesn't, so let it end here before this starts making her uncomfortable.

She has already rejected you and tried to be nice about it. This isn't something you can change. What you have control over is whether you're the guy who couldn't take a hint (don't choose this one), or the guy who had a crush on her and took a hint and was cool about it (this would be my recommendation).
posted by FAMOUS MONSTER at 4:48 PM on July 23, 2012 [7 favorites]

Sounds like she likes you as a lunch companion, and you should let anything else be until she decides otherwise, which may or may not happen. I suggest you look for dating relationships elsewhere.
posted by EvaDestruction at 4:51 PM on July 23, 2012 [2 favorites]

It sounds like she's been trying her best to be very clear that she doesn't want to date you, but still wants to have lunch. I think the time has really come to fully respect that and not keep trying.
posted by cairdeas at 4:54 PM on July 23, 2012

At one point, I asked her if she was seeing anyone, to which she replied "No, are you seeing anyone?" I said no, and that I was interested in asking her out, but was not doing it right then and there, mind you.

Yes, you have certainly been rejected. Just a note for next time, however: when asking someone out, shit or get off the pot. No one wants to have a conversation about maybe going out a sorta date some time in the future kinda .
posted by griphus at 4:59 PM on July 23, 2012 [8 favorites]

Dude, drop it. If you are in the U.S., your HR department would not be happy to hear that you keep asking out a coworker who has clearly told you no.
posted by Wordwoman at 5:03 PM on July 23, 2012

Are you in the U.S.? Yeah, you could have handled asking her out better and she could have handled rejecting you better, but you did ask her out and she did reject you. Take it as a no. If its not a no, the ball is clearly in her court.
posted by J. Wilson at 5:06 PM on July 23, 2012

Okay, anonymous off -- this is the OP.

To be perfectly clear, I have NO intention of asking her out again. Sorry for being unclear on this point -- I'm looking for advice more on how to proceed with the existing relationship, not whether I should actively pursue a romantic relationship.

Thanks for the responses so far, but please keep in mind, this is not an "I'd like to ask her again thsi week, please give me permission" query. I should have made that clear in the original post, and apologize for not doing so.
posted by slatejunco at 5:10 PM on July 23, 2012

Have you read The Gift of Fear? (You're on MetaFilter... you're going to have to suffer through being told to read it again and again until you do.) Short summary:

- Women are taught from a young age that they have to be nice and can never say no unequivocally

- Therefore many women when they mean no unequivocally, will say no with some kind of qualification ("I'm not interested in a relationship right now," etc etc)

She more than knows that you like her and that you are single. Ball's in her court. "Persistence" is disrespectful.
posted by telegraph at 5:10 PM on July 23, 2012 [5 favorites]

Okay, can you be cool around her? Like, not obviously crushing on her? If not then these lunches are a bad idea and I'd dial things down to coworker status. If you can be cool, then just...be cool. Act like you would with a dude.
posted by the young rope-rider at 5:14 PM on July 23, 2012 [3 favorites]

Im just going to go out on a limb here and go completely against the prevailing opinion of the posts here. Yes you asked her out, yes she said no, but if she is fun and interesting that doesn't mean you cant keep having lunch with her. When you asked her out, she didnt say "no Im not interested thank you very much," and when you asked her if she was seeing someone she asked you right back. If I was in the same circumstance I would just keep having lunch with her, and DO NOT ask her out again anytime soon. Although she may be interested, nothing is going to happen anytime soon. My advice to you would be to keep making up excuses to see her (with her explicit approval of course), but make no move. Get to know her better, and let her get to know you, but have NO EXPECTATION of it going anywhere romantic. On the other hand dont give up all hope, just keep any relation between the two of you friend-like in nature.

I was in a situation very similar to what you described (only she was my boss :D) and 6 months after we started dating, she said that it was like a month after we started eating lunch together that she started to think about me "in that way."
posted by KeSetAffinityThread at 5:17 PM on July 23, 2012 [3 favorites]

Just let the asking out part become a thing (or things) that Did Not Happen. Scaling back the lunches is probably a good idea, I would recommend, but it's not essential if you're both committed to Did Not Happen.
posted by skbw at 5:26 PM on July 23, 2012 [1 favorite]

The first time you told her how you felt, it was bad -- you said you had to get back on good terms. This time, you asked her out, she said no, but still wants to have lunch with you. So that's very different. But a lot hinges on how she said she wants to continue eating lunch with you. You said you "found out" - which means what? Is it like she feels bad for turning you down? Then you should back off completely.

It's a little weird that you asked her to lunch the day after she turned you down. That's potentially pressuring. Your perception that you still might have a chance might be her trying to be tactful. Rather than just closing the door, she's saying no but leaving it a little bit open. The message isn't "I'm not sure, keep knocking," it's "Walk away and save face by pretending you just changed your mind." That's often what an ambiguous rejection means.

On the other hand, if she really is as good at setting boundaries as you say she is, I'd expect a much clearer no. Introverted people have a higher tolerance for being perceived as unfriendly -- it is a common stereotype -- so when introverts receive unwanted attention, they often withdraw quickly and decisively. If she's not doing that, then it might be a good sign.

But in the end, this is irrelevant. What matters is that you aren't moving at a pace that she's comfortable with.
posted by AlsoMike at 5:56 PM on July 23, 2012 [1 favorite]

Take her cue - she's not interested in dating you -- yes, that was a rejection, and I'd take it as final -- but she wants to be friends. Can you do that without wanting more and implicitly/explicitly expressing that you want more, without expectations beyond friendship? If so, then keep having lunch.

To be honest, though, the fact that she has both indirectly and directly shot you down more than once and are kind of still wondering about it (whether you rushed it or whether you've been rejected) makes me think that you should back off until you are truly ready to accept her answer. I have the impression that when you say "I'm not asking whether I should actively pursue a romantic relationship" you mean whether you should keep hanging out with her hoping she may change her mind, and I definitely think no to that. Just because she may enjoy not eating every lunch alone isn't enough to hold on for.
posted by sm1tten at 5:57 PM on July 23, 2012 [1 favorite]

Don't you know people you would enjoy having lunch with, but wouldn't enjoy dating? Perhaps she feels that way about you. It certainly seems so from her saying "Yes" to lunch and "No" to dates.
posted by Sidhedevil at 6:03 PM on July 23, 2012 [1 favorite]

Here is an interesting article on this subject, which says basically, that she's probably just not that into you, on a purely population level anyway.

Which doesn't rule out her discovering that you're a wonderful person over the course of several lunches without pressure, and then falling for you at just about the same time you completely and totally fall for someone else....
posted by Capri at 6:07 PM on July 23, 2012

She expressed concern about being coworkers, and joked that maybe after a couple more conversations, I'd find some reason not to like her as much. It seemed promising.

To me this sounds like she was letting you down gently by using self-deprecating humor. Probably a nice gal who doesn't want to hurt your feelings outright and if, as you say, she's the quiet type, she might just be glad for the friendship you're offering. If you're happy to relax and be friends with her with no agenda, then keep having lunch, but I don't think she's being unclear about not wanting to date.
posted by pink_gorilla at 6:10 PM on July 23, 2012 [2 favorites]

You can avoid skirting the line between persistent and pesty by avoiding both of those adjectives completely. Don't persist. Don't pester. She knows you're interested, she's a grownup, she can approach you if she wants.

When you are in that crush headspace, it can be really hard to gauge the relative flirtiness / aggression of your behavior. So rate your interactions with her against how you would treat another coworker you are not attracted to.
posted by bunderful at 6:14 PM on July 23, 2012 [2 favorites]

I had a coworker make a similar soft-handed attempt last year. I rejected him, nicely. He asked me out again, and I said no. And we are not particularly friendly, and I find his attempts to hang out, offers to help me move, etc. profoundly annoying.

Don't ask her out again, and as you're probably not acting like a normal human being when you're having lunch with her, so I suggest you back off.
posted by ablazingsaddle at 6:15 PM on July 23, 2012 [3 favorites]

I'm looking for advice more on how to proceed with the existing relationship

Cancel lunch plans. Make up an excuse. Let her be the one to ask to do lunch again, and if she doesn't, then let that drop. Only be around her as much as is necessary for a little while and be cool when she's in the same room; don't be flirty or overly complimentary to her. In time this will blow over, and at worst she will remember you as, like I say, the guy who had a crush and took a hint and was cool about it.
posted by FAMOUS MONSTER at 6:20 PM on July 23, 2012 [7 favorites]

I wouldn't avoid her and cancel lunch - then you're the guy who just wanted to go out with her, and wasn't interested in being friendly when you didn't get what you wanted, which is kind of jerkish. If you can be friendly, without pining, or gazing soppily at her while she eats, you should totally continue to lunch with her - you like her, right? So I hope that we can continue to be nice to people we like, even when they don't share our romantic intentions.
posted by woolly pageturner at 6:37 PM on July 23, 2012 [6 favorites]

Go out to lunch a last time. Then, don't ask her again. On every level, the ball is in her court.
posted by Ironmouth at 6:41 PM on July 23, 2012 [5 favorites]

Oh yeah, I should have been clearer - Don't avoid her, just don't make any special effort to be where she's at, basically. But be perfectly friendly.
posted by FAMOUS MONSTER at 6:56 PM on July 23, 2012 [1 favorite]

Don't cancel the lunch plans. That could easily come off as petulant.

Go to lunch, be friendly and normal; and don't ask her again. If she asks you again, then yay, you're on your way to being friends.
posted by fingersandtoes at 6:59 PM on July 23, 2012

Nope. Do not pursue. Go to lunch with her as a friend. Don't ask again. If she wants you, she will come to you.
posted by heyjude at 6:59 PM on July 23, 2012 [1 favorite]

To be clear - go to this lunch you have planned, but don't ask her to lunch again.
posted by heyjude at 7:01 PM on July 23, 2012 [1 favorite]

Cancel lunch plans. Make up an excuse.

Agree with cancelling lunch, but don't make up an excuse. Honesty is good communications practice. Be like, "Ellen, I really enjoy having lunch with you and would love to continue doing so. However, I just asked you out, and I'm conscious that these invitations may make you uncomfortable for feel pressuring, and I don't want that. So, if you want to have lunch with me, any old time, please ask. It would help put my mind at ease, thanks."
posted by smoke at 7:11 PM on July 23, 2012

Don't say that it would help put your mind at ease. That's putting pressure on her to ease your mind, which is not her responsibility.
posted by pineappleheart at 7:38 PM on July 23, 2012 [4 favorites]

Her "joke" that after a couple more conversations you will find reason to not like her could be an important clue. I was very private at my job. I didn't want people to know about my medical situation. And I was molested as a kid. Even after therapy, coming to terms with my own sexuality, etc, I still tend to feel like men won't really like me once they get to know me better.

Let me suggest this: Prove to her she is safe with you. Prove to her you will respect her. Prove to her she is safe and accepted whether or not she dates you. Expect it to take some time to win her trust. Don't push. Make sure she knows the door is open. If she is interested, let her come to you. Make it possible for her to do that. Make sure she is comfortable regardless of whether or not this leads to romance. That should preserve your work relationship and should leave the door open for romance if she wants it.

I say this in part because I had an unpleasant run in with a man at work and I told him in no uncertain terms that he was not to talk to me that way. I spent the next few months bending over backwards to make him feel respected and prove I was not a threat to him. He eventually got over it. So this will preserve the work relationship, even if romance is off the table.
posted by Michele in California at 7:48 PM on July 23, 2012 [2 favorites]

Lunch is sort of moot at this point -- there's nothing to cancel. We met today, and for the third time, I failed to make a slobbering fool of myself. Enjoyable conversation, good company, no more, no less. Left it up to her to ask. Hope she does, but we'll see.

Bunderful's phrase "crush headspace" struck me as particularly interesting, and something I'll have to think about. Part of me wishes I had asked the question differently now that I have that phrase: "How might still being in a crush headspace be distorting my perceptions of the situation, even after clearly being turned down? And how do I get back to a more level, relaxed, organic friendship with this co-worker, and leave it gracefully in her court?"

Well, live and learn -- sometimes I need to learn a new term before I understand a new idea.
posted by slatejunco at 7:51 PM on July 23, 2012 [4 favorites]

I agree with those who say that you should proceed with the planned lunch. At the lunch, act like you did before, don't make any mention of your asking her out, even in a joking or innocuous way. After that, the ball's in her court; let her invite you to the next lunch, if there is one.

I wouldn't cancel because a) it could make you look petulant, like you want to get back at her for not wanting to date you, and b) maybe she actually does enjoy having lunch with you, and if you're cool with just being lunch buddies, then, cool. At the very least, a cancellation on your part could easily be misinterpreted as her rejecting you being A Thing, which might make things awkward around the office. So, yeah: go forward with the planned lunch, be friendly and polite, and let her take it from there.
posted by breakin' the law at 7:51 PM on July 23, 2012 [1 favorite]

Lunch is sort of moot at this point -- there's nothing to cancel.

Guess I should have read the new comments then...anyway, it sounds like you are handling the situation just fine.
posted by breakin' the law at 7:54 PM on July 23, 2012 [1 favorite]

slatejunco - how to proceed with the existing relationship

I was you.

I accepted that she was not into me that way. Friend zone. Imprinting.

She was an awesome person and I deliberately made the effort to acknowledge when she was awesome and when she was not. She's freaking awesome. Except for when she wasn't. The crush fades, especially when there's no physical/psychic reinforcement for it (ie, physical/communications detachment).

Still, it fucking sucks. And it became an uncontrollable ritualistic mental self beatdown whenever I was trying to interact with other people. It was awful.

Pursuing other available potential mates helps, and success helps TONS. The hard part is the success aspect, but that's a different ask.me.
posted by porpoise at 8:49 PM on July 23, 2012

Don't say that it would help put your mind at ease.

You're completely right, what I really meant was "Help put my mind at ease that you're not feeling pressured or uncomfortable to come along to lunches".

But that all said, reading the updates, I think you're all good.
posted by smoke at 9:30 PM on July 23, 2012 [1 favorite]

In work and school settings I've always come across as The Shy and Mysterious Private Person, so I can give you an explanation from my point of view. Of course I am not Your Mysterious Private Person™, etc etc.

In my case, any potential relationships (whether friendship or dating) are entered extremely cautiously. Since you describe her as shy and private, this usually goes hand in hand with an introverted personality. Too many times have I formed friendships with people who drained the living daylights out of my energy with needing constant interaction, or dated people who found me attractive in the beginning but end up bewildered by the pace at which the relationship progressed. This has lead me to keep people away at arms length locked-castle-tower-surrounded-by-a-moat-filled-with-alligators length.

I enjoy laying groundwork with people, really getting to know them and their personality on an honest level (versus a "I want you to like me!!" or "I want you to find me attractive!!" level). It's only through regular and small interactions that I can really get a sense of someone; sometimes it'll spark the tiny beginnings of a friendship, and sometimes it just fizzles out.

Not to say I don't ever date people or make friends on a manic whim, but those I do fizzle out Q U I C K L Y and with bad feelings all around. If someone I thought was a generally good person that I work with confessed feelings toward me, I would be even more super extremely cautious about building any kind of relationship (outside of work) with that person, because as history shows us: dating coworkers is taboo for a reason. If someone that I worked with confessed feelings towards me I would feel extra anxious because I wouldn't want them to think I was leading them on when instead I was honestly trying to get to know them better.

So, if Your Mysterious Private Person™ were me, I would not say this situation is hopeless. It would be prudent not even to force a friendship on her, but always acknowledge her presence and not put her on the spot with too much extra attention. Hope this helps :]
posted by french films about trains at 12:01 PM on July 24, 2012 [2 favorites]

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