How to Pick Up Men. Avoid staring into the eyes without a break. Which chicago chat rooms she doesn't have. If he's been checking you out the whole time, be bold. Let's be realistic here. Think her passion for hot dogs and minor league baseball suggests just the kind of chill, fun-loving girl you've fantasized about dating? Make eye contact. A two player video game is too. Stay cool. Invite your friends to go to the beach with you and tell him that his group can meet up with yours. At the end of the day it is a bit of luck and a lot of probability. Be natural. If she doesn't start showing any signs of accepting you, you need to find some sort of middle-ground or understanding with your boyfriend as to how to handle things. Don't be too forward: you're a human, not a god. If she says no, don't take it personally. People are very unreliable self-reporters. Don't feel guilty because you don't want to; it's your body and your choice. It's hardly going to win you a prize if she can't stand being tickled and you won't stop.