I think I know the type of girl you're talking about. This is what you need to do, and trust me I know my stuff.
1) Have a woman cut your hair and go and pick up some paul mitchell. Then go hit the tanning bed.
2) Go hit the mall, and don't come back until you've bought 3 polo shirts that are a little small... a white, striped, and a pink one.
3) Get a razor blade and cut holes in all of your jeans.
4) Buy an ironing board, iron, box of condoms and 5 cans of spray starch at walmart.
5) Heat up that iron, lay a polo out on the ironing board with the front down and collar up, then put that iron in the right hand and a can of spray starch in the left. Get to work.
6) Repeat step 5, 2 more times. And shave your balls.
7) Put your pair of ripped up jeans on, then your white polo... then your striped one... then the pink one on top of that.
8) Call her up and tell her you're taking her to dinner at the local Italian Bistro. Then put 3 condoms in your glove box, and then go pick her up.
9) When you go to her door to pick her up, shrug your shoulders a bit, and those 3 collars should go up one right after the other, pop, pop, pop.
10) While at dinner tell her that you saw an ad for hollister models while you were at the mall shopping and you think that she should check into it...
The rest of the night is history.