When it comes to hitting on girls there is no right thing to say, except what you feel like saying. The problems come when you try to filter or modify your behavior for their benefit. The dude who comes in and sweeps your set does the opposite. He probably doesn't care a what people think and will often make outrageous comments, or just be really, really candid to the point that it's charming, funny or at least interesting. To wit:
Intellect without candor BORING
Sure you can make small talk and maybe even wow people with a few factoids. But unless you speak from your gut, and sometimes without deliberation, you just feel scripted. The real key to keeping people engaged in a conversation is hardly ever the subject matter, it is YOUR emotional perception of it, the way you paint the picture.
I dont know if you have seen this, but a great illustration of what I'm talking about can be found in an interview with Dave Chappelle on Inside the Actor's Studio
http://www.youtube.com/watch?v=nihoa4z8wgI
The actual interview begins at 6:00 so feel free to skip ahead of that long intro. Watch how Dave responds to very mundane questions. He's not trying to be funny at all. At many points he is being dead serious or just making idle observations, but people laugh or chuckle because he has an ironic way of looking at the world.
You want to hook people? Look for irony or contradiction, which there is always plenty of. Here is another example from a recent chat of mine with a girl I am warming up for a first "date":
ME: *poke* what you doin beb
HER: research for a paper on tax laws, its due tomorrow
ME: sounds terribly exciting
HER: oh its a hoot alright lol
ME: I was gonna ask you to join me for something more tame, a few drinks and whatnot
ME: but now I see you are too much of a wild party girl. I'd never be able to handle you.
HER: ha!
HER: you have a lot of nerve fella. who says I want to be handled?
ME: nobody, at least not with words
ME: but there is a certain look in your eyes that you get which gives me that impression.
HER: what impression?
ME: That you are tired of having to multitask all the time and be in control
ME: And maybe you'd like to let someone else drive for a bit so you can let your hair down and be the tax-tallying wild woman that you are.
HER: lmao
ME: Anyways I know you are busy and I don't want to be a bad influence so keep studying. We can catch up later.
ME: Good luck on your paper
HER: hey not so fast there. what if i feel like being naughty tonight?
ME: Well that means I'll be picking you up at 10 and you should wear something nice.
HER: dont I always?
ME: True, but I want you to go all out tonight. Impress me
HER: ooh i do love a challenge.
ME: Then it's on. Just one more thing
HER: ?
ME: Wear your hair up, it makes you look more elegant.
HER: will that be all mr stylist?
ME: For now - I gotta run so see you at 10. Don't be late!
HER: k, see you later hun xoxoxo
Intellectual Breakdown:
Notice how I poked a bit of fun at her boring work by painting it as wild excitement. The contrast is out of place and therefore humorous. Also notice how I took a leap and told her what I thought she was thinking. That's called cold reading and it's not always accurate when you are starting out. But over time you do learn to read people and you will get some strong reactions when they think you see through them (even though you are just reading body language and situations more than anything.)
Also notice how I lead, steering the conversation where I want it to go, and being just a tad bossy - even going so far as telling her how to dress. You'd think she'd be offended, but in practice women really like it when a man imposes some standards and encourages her to look her best. Bonus points if you know HOW to make her look better.
Also notice how I am not sweating this chick. She is busy doing something important so I get a few lols in there and then excuse myself and give her space to miss me. THAT is when she indirectly asks me out. You see how this is working so far? Worth noting too is how I ended the interaction and didn't try to play chat game with her. I'd rather warm her up in person so chat is just a tool I use to close the deal. Don't fall into the trap of over-gaming girls via phone or SMS, it's always better to leave them wanting more of you to build the anticipation. Do the bare minimum to pique interest and settle on a time to meet.
Lastly, and this is very important. BE PATIENT. These are skills you won't develop over night. You are on the right track and probably ahead of where I was at your age, so just keep hanging out and learning the social ropes. Don't hate ont he guys that have all the attention. PAY ATTENTION to them, observe listen and learn. Hell, befriend one of them and make him your wing man. To get good at anything takes practice, persistence and humility
Good luck youngblood. May the Suave be with you