I randomly went up and introduce myself to some random chick and started hitting on her at a bar last Friday. It probably won't seem like a big deal to most of you, but I'm trying to step out of my shell. If you met me now, you probably wouldn't know that I had one, and it never was an extreme case by any means, but I'm trying to be more extroverted at any rate. I had seen this girl the previous week and at the bar and wanted to do it then (because her and her girlfriend were standing right next to us for at least an hour), but I balked. This week, she and her friend were approached by a below-average group of guys and sat down at a little table with them. I waited until she went back inside the bar from the back patio to get a drink and just walked up to her and said jokingly, "You girls look like damsels in distress." Haha. I guess that's all I could come up with. She agreed and we started chatting. Long story short, I (and my buddy joined a bit later) chatted her up for most of the night. At the end of the night, she was reeeally hesitant to give me her phone number, and took mine down instead (she still hasn't called...hehe). My wingman thought her behavior was somewhat unprecedented since we had a stellar conversation for most of the night. Oh well, can't win 'em all I guess. Another thing that was odd was that she gave me her business card around 12:30pm (we left at 2), but it didn't have her cell on it. Also, I still have some Arabic money in my wallet from my stint in the middle east and gave her a small Arabic note, with which she replied, "What am I supposed to do with this?" I usually get an, "Oh, this is so cool, thank you yadda yadda yadda." Hehe, maybe she was just nervous? She held onto it a while and didn't even want to put it in her purse. One thing that i mentally solidified that night is the fact that it's easier to approach a girl when 1) She's not with girl/guy combos 2) She didn't come with a large group of friends who only have a cohesive interest in each other 3) You're with a wingman and she's with a friend (2 on 2) 4) They're not total bitches 5) You have a sense of empowerment over the encounter I don't have a problem approaching hot women, but if they're in a group of friends or enveloped in a conversation and have a shield around them, I usually don't think about approaching them. Anyway, sorry for that side note. The aforementioned lass was probably a 6-7/10 in my book, although I have drastically different versions of hot than most of my friends. I thought I could go in for an easy kill, but I don't expect her to call though. We'll see! We definitely weren't highly compatible, but I just wanted to see if I could pull this off. I got a lot of confidence from browsing the Vag late last week and just decided, "F it, Let's do this." I'm trying to execute a small paradigm shift in my personality, which (apparently) currently includes being too cynical and condescending towards women (and men). Sometimes what comes out of my mouth doesn't reflect what I believe my inner personality wants to convey. I think I'm a softie, but often come off as a discerning prick. As a final note, does anyone have a recommendation for a book on engaging in conversation, the different elements of a conversation and keeping someone interested in a conversation? I'm sure there's books out there, but I don't know where to start. I'm interested in how my conversation and choice of words affect how I'm perceived by others.