I'll admit, I'm not exactly the king of hitting on women. My big problem (or advantage) is that I generally don't have any interest in someone until I've known them for a few weeks, at which point it is a little dangerous to hit on them.
That said, I've been called a 'flirt' several times. Nngwa? Presuming that my general approach to these sorts of things is, in fact, flirting, I will proceed to give hints. Here is my ivory-tower theory on FLIRTING.
I'll be approaching this from a 'guy hitting on girl' standpoint, but it should apply equally well to any sex hitting on any sex.
Universally, there are two ways that guys screw up when hitting on a girl. They either try too hard or don't try at all. Both of these efforts are doomed to failure.
It is a widely distributed meme that between 86% and 96% of the impression you make is in your body language, your vocal tone, your power tie - anything besides what you're actually saying. This was my first tiny window into the sultry world of The Theory of Hitting on People.
The next clue on my path was the immediate dismissal girls give any guy who comes on too hard. These two clues quickly combined into one directive - pickup lines are useless. If you're a desperate, pathetic tub of a man, no pickup line save ones that involve $40 drinks are likely to succeed. Because you are RADIATING SUCKINESS.
Think of it this way: every time you hit on a girl, you are offering a trade. Your time for her time (usually). It's like a marketplace. You're trying to convince a passing prospective purchaser to buy your crappy stuff... but you aren't able to lower the cost of your stuff, because she's paying in time.
So the deciding factor, like in many things, is simply supply and demand. She values her time at a certain level. She values YOUR time at a certain level. In most situations, if she thinks your time is worth at least as much as hers, she is happy to flirt with you and, in all probability, persue some kind of a relationship.
When you approach a situation from a 'desperation' angle, you are offering her a LOT of your time. A large supply without a change in demand means a radical drop in price. Your time becomes WORTHLESS. So she's not going to spend HER valuable time buying your WORTHLESS time.
I think that's why I've been called a flirt so many times. I have no intention of dating them, or screwing them, or any of that crap. I'm not offering them much time at all - just the moments they're taking as they talk. This means I'm not degrading the value of my time.
I suppose you could try to INCREASE the value of your time in this way, but unless you're very bright, all you'll be doing is increasing the transaction cost, and if you push it too high, she'll just assume you're either uninterested or an asshole.
Hence the first rule: Don't try to get her to invest her time. Stay in the present, not in the future. Sure, your goal may be to date her or sleep with her, but the way you'll do that is by making her realize that YOUR time is as valuable as HER time. Once you've established an equal or favorable trade with your conversation, you can broach the idea of a larger investment in the future. If you can't establish that value, consider it practice and move on.
There are many ways to make your time valuable, and all of them boil down to the things you do INSIDE THAT TIME, as they relate to HER. Sure, she might be impressed that you make mucho moneys, but you can wait until she asks. Your time is better spent trying to make her feel that HER time is valuable.
Hence the second rule: Your best shot at increasing your value is to increase her value. Not in relation to yours - don't talk about how much better she is than you. Just convince her that her time matters to you, generally by asking little, vaguely personal questions and offering cheerful commentary. The best balance is 50/50 of her talking to you talking, according to lore.
Remember the golden rule of chatting with people: People feel good when someone asks interested questions about them. That's probably the most important thing you can learn in this post. That's your best bet at increasing her value and, in turn, your own.
Of course, even if you do that, you may run into quite a lot of flat rejections. Why? Because your time is STILL worth less than her time, even undegraded. She's a beautiful girl who gets a lot of offers, you're the overweight guy who likes computers. Your time is worthless.
So you have to fix that. The easiest way to fix that is to hit on girls in your beauty bracket. If you're handsome, hit on the pretty ones. If you're not, restrict yourselves to the less attractive ones. That said, the less attractive ones are just as good a catch. Do NOT go after the less attractive ones after failing at a pretty one. START in your bracket, or they'll be offended.
Those are really the only rules I can give you at the present time.
I can't tell you how to make a good first impression. As my friends will tell you, my first impressions vary between "Spectacular, Spectacular!" and "Hannibal Lector", apparently at random. My strength lies in trying to repair the damage I did during first impressions. (Woefully, first impressions ARE the most important, and if I hit the Hannibal, there is no recovery.)
Unfortunately, the strength of my comeback game is not very impressive, and it's entirely natural. There's no skill involved.
If you go about looking for advice on hitting on girls, most of it is common sense. The rest of it is obviously to increase the value of your time, usually by providing a service ("Your eyes are like the Caribbean ocean") or by humor ("Your eyes are like dank pools of crabshells"). This should allow you to consider any dating advice you're given under a different light.
That's it. If that helps you in any way, let me know. So I can be STUNNED. After all, I'm making this post entirely on the basis of half a dozen girls I hardly know calling me a 'flirt'.