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If women smell any kind of desperation on you, it's over. Especially if you've been friends first. Then they know you well enough to be able to pick up on it better.
Seriously, the best pickup line in the universe is, "Hi, my name is _____, what's yours?" And usually the best follow up is something like, "What do you do?" and if she asks if you mean for a living or for fun, say "Either one." or "Whichever one's more interesting." or "Whichever one is a bigger part of your life." Don't think "Oh man, I need to ask her out." Just say hi. Talk. Ask her questions, answer some of hers. If she's not your type, or if she has a boyfriend, then it's cool. If she's not interested, that's cool. There's that old saying, "You find it when you stop looking for it." That only becomes true because when you're not looking, you're not trying to force anything. So it's more likely to happen organically.
Confidence is really the key. Confidence in the fact that it really won't matter too much if she says no, or if she's got a boyfriend. Confidence to not feel embarrassed by asking her out. It almost takes a little bit of apathy about the whole thing to make it work really. As long as you know that there's nothing lost by starting a conversation or asking someone out who you've known for a while, that's the first big hurdle right there.
There are, of course some basics once you get past that part: Make eye contact, but don't stare. Talk, but stop and listen too. Act casual. Act normal. Be yourself. These suggestions all seem obvious to some guys, but to others they're not. A lot of guys have been given the mistaken impression that there's a 'right way' to do things, that they have to do certain things to woo a woman. Which is totally bogus. The right way depends on you, the person you're interested in and whatever the dynamic is between the two of you. It's never the same twice. Don't force anything. If you're stuttering and stammering, not only is that a big sign to her that you're not confident... but it's also a big sign to yourself. Don't get me wrong, I'm not telling you not to push yourself. If you don't push your limits, you'll never move those limits farther away. But there's a difference between pushing and forcing.
Also on the aforementioned confidence note, the reason a lot of nice guys find themselves lamenting the fact that girls end up with 'assholes' and not 'nice guys' has nothing to do with whether or not a guy is nice. It's about whether the guy is secure and confident enough. Nice guys tend to let people walk all over them... assholes don't. The nice thing about it though is that it's entirely possible to be confident AND a nice guy. You can keep the good qualities of both kinds of guy. I don't know if that's a trap that you fall in, but even if you don't, I'm sure there are other people on the forum who might benefit from that. :)
Another way of showing confidence: Joking and/or playful teasing. That's another reason a girl will gravitate towards the 'asshole' and not the 'nice guy'. Nice guys are usually too afraid of hurting people's feelings, or trying to be nice, or trying to compliment a girl to tease. As long as you know where the line is so you don't actually hurt someone's feelings, a little teasing is good. It's a very deeply ingrained way of letting someone know you like them (think back to how it worked on the playground in elementary school.), while at the same time it shows that you're confident enough to joke and take that slight risk that you just might offend them. Find a pet name that might annoy her a little and use it now and then. Ask a girl her age, then when she tells you and asks yours say something like, "Old enough to know not to answer that question." :) Just some friendly ribbing, nothing more, nothing less. I've actually heard it described as "treat a girl like she's your bratty little sister." Which sounds odd, but it's a good way of showing that you're comfortable and confident, while at the same time showing that you're not a pushover. Buying a girl flowers, telling her how pretty she is... these are great ways to get rejected. Talking to her like a normal person and not treating her like some prize you want to win, great way to not get rejected. :)
Also, as you noted, it helps to just be around singles. I don't have much advice there, I've got the same problem myself right now. Between the fact that I don't have much cash to spend going out and doing things and the fact that I'm working the night shift, so I'm awake when everyone else is asleep and vice versa, I haven't been able to get out and meet people lately. All I can say there is get out and do things. Preferably things you like, so that you will gravitate towards like-minded people.
It also helps if you keep your life interesting. Not saying you have to go and climb the nearest mountain or learn how to do magic tricks, but if you can't keep someone interested in your conversations, then odds are you're not gonna get a date out of the deal. :) But make sure you don't try to show off any skills, talents or interests you have though... but rather try to entertain with them. There's a difference. The former gives off an impression of sad and desperate, whereas the latter just makes you interesting and fun. And when you're entertaining, it isn't just focused on one person. If the things you do can't be demonstrated, then learn how to tell good stories about them.
Long story short: Don't worry. Take it easy. Be yourself. For every action there is an equal and opposite reaction, so if you push too hard, she'll pull back. But sometimes, if you pull back, she just might push forward. Don't wait your turn, just go out and see what's out there. At the very worst you'll end up meeting people and making a few new friends. At best, well, it could end up even better than you'd think.
Best example from personal experience I can offer is from back in high school. Back when I was in high school, my stepbrother was only a year ahead of me. He was constantly chasing after girls, buying them flowers, pushing himself forward. I was always hanging back, and just relaxing. I was myself around people, and it didn't matter if it was a guy or a girl or a teacher or a student. I was just myself. He never got a single date in high school. Not one. He ended up going to the prom with a friend. I averaged one girlfriend a semester. (And that's with block scheduling at our school... so two semesters a year.) I went to the prom with a very pretty girl who, until she met me, hadn't even been all that interested in boys. (or at least any in high school) And I can't even blame it on good looks. My freshman year I was scrawny, by my senior year I was a little bit overweight, and during the time in the middle I had horrible acne. All I can blame it on is the fact that I did what I wanted to do, and the kind of girls who would be interested in me are the same kind who would be interested in the things I liked doing. And I treated everyone the same way. Made the same jokes in front of girls that I liked as I would in front of people whose opinions I didn't care about.
Heck, I can't even blame it on my good grammar... as you can see I have a tendancy to have way too many run-on sentances. :)
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