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Good perspectives. I think I'll just stick to my natural sense. Is it crucial that it's funny? What if I say something slightly arrogant but with a smile and in the right tone? Could I get away with that?
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Most girls in your peer group are so insecure, you probably don't even realize it...damn, I didn't when I was your age...you definitely have a leg up...

Dude fucking share you're experience from wiser one to younger one. How do I take advantage of that?
Hopefully out tomorrow night, I'll let my cocky side show through and see what happens.
Ha, the problem was when I was young I was just as clueless!
Young girls are always competing with each other, women in general do this, but much worse when there younger. Don't be surprised if thesed young hotties look in the mirror and think that they're fat. I had a cousin who was bulimic in college, and she was anything but fat and tremendously popular, kind of weird, right? She's the last person who I'd think would ever be insecure, but young girls just are. They also totally f with each others self-esteem and always looking for acceptance....
There's a good chance she may not even know how cute she is, and if she does, you'll definitely know.
The great thing about being young is there is so many excuse to hang out, so just be around, not stalkerish, but I'm sure you young people have certain places you tend to frequent. Definitely make her laugh and be outgoing, befriend her friends...funny thing, as I think about it, it's pretty much do what the guys on this board tell you. Most guys you're age probably don't know how to talk to girls, so just be confident (and not some frat boy idiot) and think to yourself she's probably more insecure than you are, because she probably is.
Women like attention, young insecure girls, love it - also, being able to express yourself without immature fart jokes and whatnot will get you far as well; I'm being facecious, but I think you know what I mean.
Do I make any sense? Sorry if I don't, I'm trying to think how it was to be 19 again.
(oh, get a nice pair of shoes also!)
