Bill, 32, is like many single guys who find the dating scene intimidating. "When I see a woman that I'm interested in," he admits, "I freeze up because I have had a lot of bad luck with dating. I don't know what to say when I walk up."

Dylan, 11, is unlike a lot of boys his age -- he has no problem talking to the ladies or dishing out dating advice to kids and adults alike. "If one of my friends was really shy," preaches Dylan, "I would say just have confidence in yourself -- think that you're going to get the girl and it usually works."

The little ladies man agrees to be Bill's wingman to see if he can help get his new friend's mojo back. Check out the video to see the duo workin' it at the mall!

Back in the studio, Bill shares what he's learned from his pint-sized tutor. "As adults, we over-think and we analyze, we get jaded -- whereas a kid, he was like, 'Dude, just go for it! What's the worst that can happen?'" Dylan says he's ready to let Bill lose into the dating world on his own -- and he even found a local girl in Rach's audience for him to go out with!