"We were both like, 'Who is this guy that's always got girls?'" Delgado, now 28, says of meeting his "wingman" and Hills costar Jenner. Since pairing up in 2004, the pals admit that only once has a girl come between them. "We went on a boys trip to Miami after he broke up with his girlfriend," says Jenner, now 25. "All of a sudden, they rekindle. Next thing you know, I'm in Miami by myself. I had the couch. It was a nightmare."
Watch the wingmen dish on their pickup tactics in exclusive video of their PEOPLE shoot!