I agree with most of the other posters itt. The first half was pretty good, then you made it weird. The first line I thought was kinda creepy was this one:
Quote:
ME: Lol sara sometimes you have to sacrifice your dignity do get what you want. You need to get an agent in toronto.
Everything above that was pretty good. If I really had to nitpick, I'd say you missed a few chances to make it more sexually playful early on. Like when you said "you should probably go to the gym with me if you want to get in shape", it might have been better to say something along the lines of "if you need help getting in better shape, I'm sure I can give you a good workout". One of my favorite techniques is to say things that have slightly sexual overtones and then, when the girl comments on it, call her out for being creepy, having her mind in the gutter, constantly trying to use me for sex, etc.
You definitely did some good things, too. I personally wouldn't have used the "you're spoiled" line, but at least you put the emoticon in there to make it completely obvious that you were joking. That's one of those minor but important things. I also really liked how you flipped the part about her turning 18 and then doing naked modeling. Pretty solid cocky/funny stuff for the first half...
HOWEVER the second half of this conversation was lolbad. Creepy, not funny, and downright weird at different times. And labeling yourself as a challenge was pretty lame. SHOW her that you're a challenge by the way you carry yourself and let her figure that out herself.
I wouldn't say you're blown out by any means. If you don't hear from her in a day or two, reinitiate with something funny and keep the conversation light with the occasional sexual overtones.