Justin Bieber Gets Flirty With Chelsea Handler

By: Robbie Daw / November 19, 2009

Justin Bieber, 15, was a guest last night on E!’s Chelsea Lately, where he shilled his new EP My World and spent about a full minute winking at 34-year-old host Chelsea Handler. Again, 15.

The creepy/cocky exchange—which included Bieber giving Handler actual instructions on how to flirt effectively—came after Chelsea pointed out that Justin probably had more important celebrity friends he could be hanging out with, like Usher and Justin Timberlake. “I think you’re a lot cooler than they are,” was the singer’s reply.

Handler  busted him on what we all think when it comes to teen pop stars—that the “Favorite Girl” and “One Less Lonely Girl” singer spends a lot of time singing about love and relationships. “Do you have a ton of experience with that kind of thing?” she asked him.

Somehow, though, this kid managed to wriggle out of her trap. Catch Justin’s response here:

The confident entertainer also admits that he asked out Rihanna. Needless to say, that didn’t pan out too well.