The first steps to any summer fling are to have fun and be yourself. But if your "self" is a person who's anxious about talking to people or afraid of rejection, throwing caution to the wind for an attractive stranger can be daunting, to say the least — especially if you're the one putting yourself out there or initiating the hookup. "If you’re shy or socially anxious it can be especially hard to ask someone out," says Paulette Sherman , PsyD, a New York City-based psychologist and author of Dating from the Inside Out . "You may already be extra hard on yourself and will berate yourself if you get rejected, further plummeting your self-esteem."