1. You Aren't Very Smooth
If "Hey…uh…how…um…I..uh….how you doin?" is how you start of a conversation with a woman you want to talk to, have a bottle of Jergens ready for you when you get home. The last thing any woman wants is a babbling moron trying to hit on her…badly.
The first step to meeting women (or having a normal human conversation with another human being) is to keep it simple and keep it at a point where you are comfortable (even if you are way out of your element).
2. You're Saying All The Wrong Things.
If you have made your introduction without tripping over your tongue, odds are you are now incoherently babbling about tartar sauce and this crazy dream you had in 8th grade. Most people are not great conversationalists, which is exactly why you should keep it basic and keep the conversation away from that new mole you found in the shower this morning.
Make small talk without making it too awkward (i.e. "Nice weather we're having). Talk about yourself. Let her talk about herself. Basic stuff. If in doubt, just think about how someone like Conan O'Brien or David Letterman conducts interviews.
3. Eyes Up Here, Mister!
If you have made it past the introduction and are acing the ice breaking conversation you are now either overconfident or nervous about screwing it up this far into the game. The one thing that is make or break at this point is body language. If you are staring down her shirt, looking bored, or are anxious to get out of there and into the sack, refer back to the Vaseline mentioned in point 1.
On the other hand, if you are still sweating nervously and fidgeting, you are already thinking about the Vaseline so you're all set.
Even if you are sitting across the table from a total bore or a girl completely out of your league, keep your head in the game, stay in the conversation, and remember that you are already halfway home.
4. You Overestimate Women.
Many guys think of women as these fairy like creatures and come up with ingenious plans to catch one. The truth is, a woman is still a person just like you or I, except she never has to do any of the heavy lifting when it comes to dating.
Even when the Detroit Lions get set to play the Pittsburgh Steelers they go into the game knowing that on any given Sunday they can come away with a win. If you're trying to get into a girl's pants and go in knowing that on any given Sunday you might actually get some, I guarantee that at the very least you will get more notches in your belt than the Lions get wins.