It's basically PLAYING the player guy, but in such an overtly way that it's funny. It works for the same reason's why cocky&funny works.
I say playing, because you don't want this to come of as genuine. If it does you'll just sound like a jerk.
I like the idea, I just haven't tried a lot of it yet. Just remember, if it gets a smile/laugh, you're doing it right. And when you get a weird face, or face of disgust, you said something wrong.
I use something like that, for example when someone is talking about some girl I don't know I always go like: "Oh cool, is she single? On a scale of 1 to 10 how hot is she?"
One time she went: "Well... she's actually 13."
me: "Oh wow, she's a 13 on a scale of 1 to 10, then I REALLY have to meet her!"
When in fact she was talking about her age.
Some great examples from the DVD that I like are:
Quote:
Her: I have a girlfriend.. she was horrible, she'd always try to sleep with all my boyfriends. Such a slag.
You: Oh, that's terrible, what was her name?
Her: Maria
You: Ok cool, you still got her number? Does she have facebook? She's not here tonight is she
Quote:
Her: I had a few boyfriends, but I'm not that easy, I'm not a slag, etc
You: Oh, you're not? That's terrible... well, what if you had a few drinks? Awww, alright...

Quote:
When she tries to raise her value and they want you to be impressed with it:
Her: I'm training to becoming an arcitect
You: An arcitect? :S What's the point? Why don't you just quit and become a stripper?
Quote:
You: Have you ever met one of those really horrible guys, who's an arsehole, who sleeps with all the girls and never calls them again?
Her: No
You: Oh, it's your lucky day, I'm richard

Quote:
You: What's your name again?
Her: Jasmine
You: I'm going to introduce you to my friends... hey mark, this is margaret.
You: Come meet my other friend... bob, come and meet nicola from pussy dot com
Quote:
Her: I really like your shirt.
You: Of course you do, you're only human.
Quote:
Her: blabla
You: Never mind that, have you ever had a fantasy about making love in a toilet in Nevada?
Basically the mindset you should be in is that you're just looking for that easy lay, and you're only interested in 1 thing: sex.
Just make sure they know you're joking, this is done by adding humour to it. Remember you want to be an "irresistable arsehole", not an arsehole.
And like cocky&funny it's a spice to the ingredient. Use it sparringly and not too much.