How to ask this guy out?

I (27F) met him (late 40s) in a work context. He's definitely funny and interesting, definitely friendship potential as well (more than relationship even), but I didn't have many opportunities to interact with him. I think I messed up, I didn't sufficiently capitalize on the few opportunities I did have to build rapport properly. From his point of view, he knows very little about me and that's probably a problem because he can't know whether he likes my personality or not. Now the short work relationship is ended, the coast is clear for a move - but I won't see him in person again.

He's been very friendly in emails, lots of emotes, but with him it's hard to say whether it's just good "customer service sense" (which he applies to everyone, including non-clients) or genuine interest and enjoyment in interactions. I'm running out of excuses for emails, so move has to happen now.

It's feeling dead in the water to me, but I might as well give it a shot. I'm just looking at the poor play-board and wondering if there's a good move somewhere that I'm not seeing. I'm thinking of an honest, direct approach, kind of sick of subtlety and "the right way" at this point.



Submitted January 18, 2020 at 12:10AM

I (27F) met him (late 40s) in a work context. He's definitely funny and interesting, definitely friendship potential as well (more than relationship even), but I didn't have many opportunities to interact with him. I think I messed up, I didn't sufficiently capitalize on the few opportunities I did have to build rapport properly. From his point of view, he knows very little about me and that's probably a problem because he can't know whether he likes my personality or not. Now the short work relationship is ended, the coast is clear for a move - but I won't see him in person again.He's been very friendly in emails, lots of emotes, but with him it's hard to say whether it's just good "customer service sense" (which he applies to everyone, including non-clients) or genuine interest and enjoyment in interactions. I'm running out of excuses for emails, so move has to happen now.It's feeling dead in the water to me, but I might as well give it a shot. I'm just looking at the poor play-board and wondering if there's a good move somewhere that I'm not seeing. I'm thinking of an honest, direct approach, kind of sick of subtlety and "the right way" at this point.
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