1. Dress up like a chick.

Learned from: Tootsie (1982)
Complex says: It’s no mystery that many women love the sensitive type, a guy who’ll listen to their woes and reveal vulnerability himself. In the Academy Award-nominated comedy Tootsie, Dustin Hoffman’s character, a cross-dressing soap opera star, gets a drink thrown in his face after he tries to pick up one of his co-stars (Jessica Lange). Rather than try again, Hoff resorts to a Hail Mary play: He tries to seduce her while he’s dressed in women’s clothing, a red wig, and pounds of makeup. If a failed courtship ever gets to that point, just call it quits, or visit the nearest barely lit urban street corner after hours. We hear the action is much easier there.