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If your boss is really trying to set you up, then have him go full steam on it, and ask her directly if she'd be interested in being set up on a date with you. I can say as a woman that if I'm not interested, it would be less awkward for her to tell him thanks, but no thanks as opposed to having to turn you down to your face if you asked directly.
I agree with this. Have your boss set it up. Since he's so interested in your love life (???)
My concern would be the woman feeling awkward working with you, and your boss, if she is unavailable to date you. If I had to turn down a date/setup with someone I will be working on a project with, I might feel awkward around them. What if there are more projects coming up?
There is this girl through work who my boss is trying to set me up with. She doesn't work with me or for my company, just a company we work with on this project (Shes with the architect and I'm with the construction company). I've only actually met her in person briefly twice, and we have occasional brief conversations on the phone related to work. Also, I will soon be assigned to a new project.
I was wondering if I should ask her if "we should get together sometime" or "meet for lunch sometime"? Would this be okay? Would you be okay with this in a similar situation? My boss actually sent her over to my office to talk about "work" the other day, hoping I would maybe ask her out. I haven't really joked with her or anything. I feel so much more comfortable asking a girl out after there is a laugh or two or some flirting. We just briefly talked about where we live etc. We don't really know each other well, but I'm not worried about the whole work thing. I just don't want her to be in an uncomfortable position of feeling weird turning me down if she's not interested.
And please, no preaching about how my boss shouldn't try to set us up or anything. I'm attracted to her and glad he is trying.
If you are interested, go for it. What's the worst that can happen? She says no and you move on. I used to care and be nervous but as I get older now, I really don't care. I met my wife online on bumble and made the move to date her. I was nervous as all get out.. but I did it.
Ask her out for dinner and no pressures. If it ends in disaster or you guys don't mesh well, oh well.. you tried. Only a couple hours left in 2019.. Start 2020 off with positivity!
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