Quote:
Originally Posted by Solecismic
I would not try to friend her, though. A friend request accomplishes nothing while giving her an opportunity to view you critically while you're not present. It takes attraction out of the equation.
If this weren't a work setting, you'd just go up to her and ask her out for dinner or something. I get the "how else am I supposed to meet someone" argument, but work is somewhat sacred because she has to be there and it makes people feel unsafe to be approached, one-on-one, at work.
I think the group approach is a good one. Be early. When she comes in, make eye contact and say something to her. If she makes it easy for you to sit next to her (or if you're already there, sitting, and she chooses to sit next to you), then you can probably suggest a later dinner date when she's leaving.
If she doesn't give you a good opportunity to sit and talk during the event, she's probably aware of your interest and doesn't want to encourage you. In that case, you're going to have to let it go.
One of the hardest things to accept about dating is that it's not like a job application. It's a convoluted, mutual dance and if a woman is interested, she'll give you opportunities to ask her out. They're not the mysterious creatures of lore that we build them up to be when we're inexperienced.
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All of this, pretty much. I'll also add that figure out your strengths/talents and play to them. Every relationship I've ever had, the girl fell for my writing first - whether it was online, in role-playing chat rooms, or in conversations via email or a messenger app, or in the simple passing back and forth of notes in some tedious situation (a speaker, sitting in the university computer lab, etc.)
My sense is that a one-on-one situation to start will be an epic tank - the kind that winds up in a Reddit subgroup or a listicle. Keep it low-key and no-pressure with a group event first. Be the one to organize it and get people to go. Wait until you've got a few yeses from other people first (including some other women). Then ask her and say, "Hey, a bunch of us are going to do X. Person A, B, C, are all already going, and I wanted to see if you wanted to come, too."