Originally Posted by SupermanwOOt
TheNoid's response was great, but I would like to add/change this. Usually you meet a girl in a strange environment: bar, work, school, whatever. Somewhere that if you are looking to take things beyond 1 night in the bedroom, it would be almost impossible at that point. Especially if you are nervous, just asking her out on a date may be difficult. Here is what I have tried: Ask her out to lunch.
Before you flame me, think about it. Its a quick way to get her number and set something up on a one-to-one basis without ANY stigma of a "date" or "showtime" situation. Then once you are semi-alone, see how you meld. OP says he is good at just talking with them but its hard to make that move. Believe me, it can be, so this method takes a lot of the guesswork out of it. If she says no to lunch, you dont have to feel that you got "shut down" and she wont tell her friends that youre some douche trying to get in her pants, etc. She will respect you as a nice guy who is also outgoing and willing to hang out with her in a realistic one-on-one setting before trying to get her on a date. You will hardly ever get rejected like this. And its basically a filter if anything. If you make it to lunch, there are no expectations except to have a good time. So if you have a good time then ask her out on a date. win-win
Usually you go out, have a good time, get to know her and then set up something for later on. Sometimes you may realize that this girl is not what you thought, and you ask for separate checks and dont schedule a follow up date. You are in control and usually in these situations its mutual. I have been at bars/parties and felt that girls are into me, only to ask them on a date get their number and then get denied the next day. It is exceedingly rare that you would be feeling mutually into each other at a lunch situation and then get rejected on the date. Funny thing is, what happens a lot is you ask a girl to have lunch with you at cafe or something and then she starts telling you about her boyfriend. Its awkward as hell for 2 seconds, but then you realize, we are just at lunch and can say oh well I was looking to take you out on a date but I see thats out of the question, or just let it go and don't hit her back up.
Try this please and let me know how it works for you. As an example I just met a girl the other night who was seemingly perfect. She was gorgeous and i got setup for lunch with her. Started talking and she was telling me its nice to hang out with a nice guy since her boyfriend was in the navy and stationed in san diego for 18 months (I'm in NC). I was a little upset/shocked at first, but we honestly had a great time talking because we were in the same profession and went to nearby schools. It wasnt a waste of time at all though. It was great company and I don't plan on calling/texting her again unless she lets me know she's calling it quits with the cadet and then I'd have a good chance at getting that date. I'm just citing this one because its the last one that happened, even if it didnt end well.
Lay the groundwork over lunch, not with a few inebriated one-liners at a bar. Its amazing how different (a lot of the time pleasantly different) over lunch than out with their friends.
PS: the reason I came up with this is that I work at a hospital at the moment. Now if I think a nurse, PT, PA, etc in my department is liking me and I ask them out on a date, that can have negative consequences if I got the totally wrong impression. It would be pretty hard to work with them or pass by them in the hallway knowing I got shutdown. However if I ask them out to lunch and they decline: no harm done. I could just picture getting kicked off the medical staff for making advances at a hot nurse, however making an offer to share a lunch with them is not at all invasive no matter how you spin it.