I have a fews words of advice for any guy who wants to pursue a pretty girl they see out, don't be shy! I have this theory I have been working on for some time now (in the hopes of getting my very eligible brother a girlfriend) and it has even expanded so far as to become a cheesy metaphor so here it goes...
The way I see it bars are the easiest places in the world to meet people, and yet too often I see nice guys in the corner staring and longing for a pretty thing in a skirt that they could easily have if they showed a little bit of confidence. So, I propose to the men out there to make a small investment. It's a relatively painless procedure and it could lead to a major pay off. Are you ready? Send her a drink. See it's very simple. You go to the bar tender/waitress and when you see your pretty lady's drink getting low you suavely refill it. I believe the key to this is not to come off too eager. You should not follow the drink into her hand, but instead maintain your position at the bar and wait. Allow the girl to assess the situation and approach you on her own accord, you might be pleasantly surprised by the results. Now there are a lot of factors leading to her decision (looks, attire, intoxication, friends, and the list goes on) so this plan can end in a number of ways.
1. The Failed Investment: I'm starting of with the worst case scenario for a reason, because I don't think it will happen and even if it does its not even that terrible. Say you send the drink over and still she feels no urge to talk to you. Fine. Don't get mad or embarrassed or even view it as a bad thing, you tried and now you can move onto someone else. Sure you may have lost a few bucks but what's the big deal. It was worth a shot.
2. The Short Term Investment: For some this may seem like the best case scenario while others might disagree but here is goes. She takes the drink and when the waitress points to you and says, "it's from the gentleman at the bar," your target sizes you up and begins the approach to say thanks. You get to talking, get a few more drinks, and then a cab back to your place (unless you and your personality get in the way at some point). You have a successful one night stand, and if that was your goal then congratulations.
3. The Long Term Investment: So everything starts off the same as the short term investment but the ending is different. When she approaches you this time you say something goofy and sincere like "I honestly wasn't sure if that was going to work." You laugh, you talk, you make yourself desirable, but instead of taking her back to your place you get her number and at a later more sober time you ask her on a proper date. Who knows you might even have a girlfriend by the end of it.
Sending a drink will show how smooth you can be and that will peak her interest. Waiting will prove your not overly aggressive, and if she's coming over than she is intrigued which should make you feel confident in yourself. Most girls will see it as a mildly romantic gesture because of it's old-fashioned nature, like something straight out of an old movie, plus all girls like the attention. She's going to be so overcome with nostalgia and shock she'll have no choice but to talk to you!
Well there you go. You have the tools now go make it happen. Remember you'll never get the girl if you don't try!
sincerely your lady wingman,
Liz