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Edited on Sun Mar-07-04 11:05 AM by gmoney
1. It seems fairly univerally accepted that a person (man or woman) "sizes you up" as a potential romantic partner within the first few minutes of meeting you. I think that's going to apply here, even though she was involved when you first got to know her. So, she's already made up her mind, and since she WAS involved earlier, it's unlikely she's thinking of you "in that way" even if she enjoys your friendship. (However, if she DOES think of you that way, once she's over the break-up, she'll probably let you know she's interested.)
2. The job situation is a big complication. If she's a project manager, and you're a programmer, isn't it likely that you'll need to work together on some projects? There's almost no scenario where you two being together is a good thing in this regard. You make your move, she rejects you - bad, plus she might sue you. You make your move, she accepts but it doesn't take - bad. You make your move, she accepts and you start dating - maybe OK for you, but will cause problems for others involved in the project, and possibly your employers - bad. About the only thing that could work is if your employer is OK with co-workers dating, and there's almost NO chance you'll ever work on the same project.
3. The Dreaded Good Friend Syndrome. Another killer obstacle... you've established yourself as "safe" -- as a friend. Almost 100% guarantee that there will be no soup for you. If you'd been the mysterious guy from the other department who had a nodding acquaintance with in the hallways with her, maybe. But not if you're the "big brother" buddy whose shoulder she cries on... you might get one night of reckless abandon if you play your cards right, but it will get weird after that, and you're back to bad career move.
4. The age thing. Sure a 30-ish guy will be interested in a 22 year old woman, but you're almost half again as old as her. You were in college when she was in 4th grade... unless she's unusual, I think she's going to look for men closer to her own age, and she's probably NOT going to be in a hurry to find a serious relationship right away.
I know, doom doom doom, coming from a guy who's not really managed to handle this situation right in his life. But if your job is potentially on the line over this, I think you're much better off with a friend in the office than an ex at your old job.
The bright side, as a friend, maybe you can ask for her help to find you a nice girl... she can talk you up so your blind date is comfortable with your qualifications, yet you remain something of a mystery man, and there won't be the employment conflicts. She might ask you to return the favor though, which could be rough if you really have feelings for her.
Just don't go all "stalker" on her. Be available, but not omnipresent. REAL bad news there.
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