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What's the Best Way to Play This?


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So there's this guy. I am 99% sure he doesn't know I exist, and I think we're probably in very different leagues. I am not used to feeling like that, but in any case... We probably have no business dating since a) he's a bit older than me and b) he and I "met" under professional circumstances. He isn't a boss or co-worker, or anyone I would see on any regular basis though.


On the one hand I'm very much the "let him come to me" type, and I don't want to break TOO FAR away from that. But on the other hand, even IF there is mutual interest, how likely is he to approach me, considering the potential conflict of interest. I guess for all the same reasons I'd be worried about letting on I might be interested in more than just a working relationship, it's very possible he's thinking the same. That is, if he is thinking along those lines at all.


An added complication; if something doesn't happen soon, it's very possible we wouldn't meet again.


So, how should I play this one? I don't want to be too over the top and risk embarrassment, or costing myself professionally... But I don't want to sit back and let things just NOT happen either, if there's a chance they could.

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hm..... i vote for asking him a work related question - something that he has expertise in, and would take him a good 20-30 minutes to explain to you... like have him teach you how to use a certain software, if that is his specialty. think about it for a while, and figure out some pretense that you can see him in his office, and see what happens. worst case scenario, he's in a relationship, and you just got a free tutorial on microsoft excel (or whatever). good luck!!!!

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Hmmm... Seeing him in his office isn't a problem. I could pretty well call him and tell him I need to see him, and he'd make himself available for me. I guess the part I need help with is, assuming that next time is the last time I ever see him (and we would be alone, that's a given) how can I let him know I'd be interested in him if he chose to take that step? Without coming off like a fool if he isn't interested!


Last time I saw him (which was also the first time) it was an hour of sitting accross from him in this back and forth interview-type deal. My stomach kept flipping. I think I must have said some stupid things, but in any case I hope he didn't notice... I just haven't really felt like that for a LONG time and it caught me off guard. He's got the most incredible smile.

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Basically, he works for a consulting firm, handling my profile, and his job is to find me work. It is very possible (if he does his job well, and if I do MINE well) I would never see him again after my initial placement. Hey, I didn't say this would be an EASY situation!


I wasn't quite sure of the vibe... Our meeting ran longer than it was scheduled to, and he rushed me out of his office about half an hour past it's scheduled end. He talked a lot, and asked me a lot of questions. But this is his JOB. He definitely wasn't as obvious about any interest as most guys I meet, but neither would it have been very professional of him to be like "hey, I know I am handling your profile but wanna go out for dinner?" A LOT of women might take offense to something like that, and it would technically be grounds for a complaint if someone was the type.


As I said, I am pretty sure he doesn't know I exist. And I probably have no business dating him anyway. But man, I never wanted that meeting to end.

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I can see the predicament he'd be in even if he were attracted to you. Can you perhaps wait until after he finds you a placement and then try to talk t him, maybe flirt with him? What would happen if your initial placement doesn't work out? Would it be awkward between you two in that he would have to work on your behalf again and it would be weird if you tried to flirt with him in the in-between time?

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Talk to him HOW? That's my whole point... And yeah, the weirdness could potentially get involved in future placements if the first didn't work out.


You may have to be more assertive with this one that a woman would ordinarily be when she's interested in a guy. I'm all for the "if he's into you, he'll ask you out" way of doing things. Ideally, that works best, but in this situation, you will need to do some nudging. Since you won't have the chance to bump into him and since it's unprofessional for you to flirt with him right now, you need to decide if you're going to go for it and run the risk of things being weird down the line. If that is what you decide, wait until you get placed, and then...call him, thank him for his work on your behalf and start dropping hints that you'd be open to seeing him. He'll get the hint and he'll either agree or politely decline.

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