I can’t decide if I should try for something, or just let it go and figure it wasn’t meant to be. And if I do try, how?

I have been on a team at work for about 20 months; about 6 months ago realized that a co-worker is really neat — kind, funny, similar life outlook, we have great conversations, etc. There are many indications that he is a gem. There are also some signs that the interest is mutual. He definitely likes me, but my jury is out as to whether he likes me or just likes me. FWIW I have always thought he was a nice guy but until earlier this year thought he was much, much younger. I am cursing the timing on this now.

For unrelated reasons I have been trying to get off this team and into another job for the past 6-7 months. When I realized I liked him I figured I could stay in touch after transferring, maybe be more obvious about my feelings, and see where it might go. Under normal circumstances I would have transferred a while ago and would have had some time to let the thing with him progress naturally and get a better idea whether it has legs, but the job market, even internally at my company, has been pretty sucky lately.

About a month ago our boss mentioned in a meeting that sweet/funny coworker is planning to move back to his home country. When we had some time alone I asked him about it directly. The upshot is that he’s homesick, he has an aging, possibly senile parent; he misses other family and friends and his work/life balance sucks in ways that it wouldn’t at home. Also, though he didn’t say it directly, he implied that he’s lonely and disappointed that he never found a partner over here in the US. If all goes as planned he’ll leave in slightly under 2 months.

In a subsequent conversation he said that the next time I visit his home city (a city I have visited several times, and love, which he knows) I should know that I have a place to stay and that he would like to show me around. So, nice that he wants to keep in touch, but…

Should I tell him how I feel before he leaves? Should I ask him if he wants to date me before he leaves? Is there any point? If he weren’t leaving I would have been happy to wait to see how things unfold, but now there’s no time and I don’t want to kick myself later because I didn’t have the guts to do something, but I also don’t want to act like a crazy person over something that may or may not have potential.

In other circumstances I might hang back a bit and see if he makes a move (and also to just let things develop naturally), but it’s hard to know if he’s not asking me out because he doesn’t like me that way, or because a) we’re co-workers and b) he’s a self-professed nerd and a bit socially awkward and c)he’s leaving the country soon.

I just don’t even know how to present what I am feeling because it comes down to, “Hi, I like you and hope that something could work out in the next 2 months that could enable us to see if anything could work out over the long term, so, uh, do you want to go get a drink?” I don’t know how to say this in a non-crazy-sounding way.

For what it’s worth, I am financially secure enough to have some flexibility about where I live and work, and will have even more freedom if a project I’m working on now pans out over the next year or so, so it’s not completely cuh-ray-zay to think that if we were a good fit, things could work out longer term, but nevertheless I feel crazy for even thinking that far ahead. On the other hand I have so much fun with him and he’s so sweet and I am going to miss him horribly when he leaves.

Believe it or not, we’re both in our forties, but it seems that one is perpetually 14 in situations like this.

Hoping you and the Nation might have some suggestions for me.

Thanks!

Midlife Teenager

Dear Midteen,

As my dad once told me when I was hopping around by the phone like I had to pee, psyching myself up to call a boy and ask him to a dance, “The worst he could say is yes.” Heh.

Okay, for real now. This leaped out at me:

…it comes down to, “Hi, I like you and hope that something could work out in the next 2 months that could enable us to see if anything could work out over the long term, so, uh, do you want to go get a drink?” I don’t know how to say this in a non-crazy-sounding way.

That isn’t that crazy-sounding, and even if it is, who cares? Okay, maybe HR cares, but that’s a short-term problem and you can find ways around it if you need to. It sort of reminds me of that line from A Tree Grows in Brooklyn where Francie’s mom says, “I hate all those flirty-birty games that women make up. Life’s too short. If you ever find a man you love, don’t waste time hanging your head and simpering. Go right up to him and say, ‘I love you. How about getting married?'” I mean, you aren’t simpering as far as I can see and I wouldn’t barge up to him at the coffeemaker with a proposal, obvi, but the “life’s too short” part is key, especially in your case. Asking to speak to him privately towards the end of the workday and saying, “Look, this is awkward, but the meter is running on your time in the country, so the hell with it: I like you That Way and I want to see if there’s anything there. Will you go on a date with me?” is going to suck and you will shred your cuticles over it, but it’s going to give you information you need. Either he’s going to tell you he likes you but he doesn’t Like You Like You, which stings, but at least you know and you can move on to the next thing; or he’s going to Like You Like You but think it’s off-putting that you got direct about your feelings, which isn’t really workable and it’s better you figure that out now; or he’s like, sweet, let’s go on a date.

And then things could go any number of different directions, but difficult though it is to resist brain-doodling about this stuff, try not to get ahead of yourself. It’s normal to do, you will do it anyway, but give yourself 30 seconds to daydream-move to his daydream country and work with him on the daydream unicorn farm the two of you own together while eating nothing but chocolate and hope, and when it’s about to get rated-R in your head, snap yourself out of it. One thing at a time. You don’t have to present your able-to-move credentials to him during the appetizer course, or make your case.

And this is the other thing: if you feel yourself having to make a case for why it could work out, or talk him into it at all in terms of taking a chance, it’s no go. If he’s willing to see where things go, and you get a good vibe, great — but if you feel like you’re in a pitch meeting, pack it in. Ordinarily I would make more of the fact that he hasn’t actually made a move as an indicator here, because in my experience, a guy who really likes you will make that known. If he’s socially maladroit, that’s the manner in which he will make it known…but it will become known. In Co-Worker’s case, it’s maybe a workplace issue, and/or a “why start something when I only have 8 weeks left here” issue, so I give that part less weight, but relationships that start out with you talking the other party into giving it a try really never stop feeling that effortful and shitty.

In other words, ‘nad up, invite him out on a Date Date, and give it a chance — but only the one chance. I can trace probably 65% of my grievous romantical errors to “the timing is terrible, but…” Sometimes, ain’t no “but.” It’s just terrible timing, and you ignore it at your peril. The timing here could lead to a wonderful connection that you’d never have forged if a ticking clock hadn’t forced you to make a move or wonder forever, and LDRs and international affairs of this type work out all the time; if you become partners, you find a way. But don’t worry about that part now, and if he’s already got his boxers in a knot about that part, get on OKCupid and find someone else.

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