Crystalite said:
But if it comforts you, a girl that does not adhere to the general rules of attractiveness will be alone as well, and often be ridiculed for the fact. And any girl not looking like Natalie Portmann is considered ugly these days, whereas for men, the appearance range is much wider.
You've been hanging out with the wrong men. Or you've just been reading the wrong newspapers/magazines. Personally I'd say that the appearance rage is a lot wider for women, or at least in terms of the girls I've dated (I've been attracted to fat women, skinny women, tall women, short women, bla bla bla). Not every man thinks like me of course (because most men are dumb), but I'm pretty sure that you shouldn't sell yourself or any other woman short because she doesn't look like Natalie Portman or whoever's fashionable these days.
So long as you have a girl has her own original hair and teeth then she's probably attractive.
Even if a girl doesn't. Hey, that's probably somebody's fetish - they could still find somebody through craigslist. Win!
As for the op, here's what works for me. When you see a girl you like and you want to talk to her; all you need to do is think like you're going to make a fool out of yourself either way. Expect to fail and the kiss'll be twice as sweet, the phone number will feel like an olympic medal. If you fail and she laughs in your face, then so what? Move on. Find somebody better and here's the thing, there is already somebody better. You know how many girls there are out there? Loads!
As for what to say, just be polite, ask her how she's doing - offer a drink or whatever. None of this 'I noticed you from across the room and think you're really beautiful' crap, trust me - she knows why you're talking to her. Also, avoid the cheesy chat up lines and cheap tricks. That old adage, be yourself, it works.
You just need to actually know who you are.
I mean, I'm an out of shape, fairly shy, nerdy type. I get so nervous when I'm trying to talk to a girl that my knee shakes the entire time, I still manage to do okay with the ladies because I can make jokes about my insecurities. There's no magic formula for confidence, you just have to get yourself out there! It gets so much easier once you start to view chatting up girls as something fun instead of something to be afraid of. Because it really is a lot of fun, even when you cock up you still come away with a funny story to tell.
It wouldn't hurt to put some time in at the gym too. You feel so much more confident after a good work out!
Best of luck!