Ashton Kutcher Once Bet A Friend He'd Date Jennifer Aniston

Ashton Kutcher is already married to a famous cougar, but before he moved to Los Angeles, he had his sights set on another older celebrity -- Jennifer Aniston.

"I bet a high school buddy $1,000 that one day I would go on a date with Jennifer Aniston,” Kutcher told The Graham Norton Show. “I was 17 years old and she was on my screensaver.”

Ashton says he actually came close once -- after meeting the famous Friend, the No Strings Attached star says he got permission from Jen's then-husband Brad Pitt to ask her out.

“Five years later I actually met her and I asked Brad Pitt’s permission to ask his wife out on a date," Kutcher said. "He was so cool and said ‘You go for it’ so I asked her and she turned me down.”

Even though Ashton is happily married to Demi Moore, who's 15 years his senior, he still hasn't given up on the dream of winning a date with the famous Friend.

“Now we’re friends so it might still happen, but now I have to ask Demi’s permission and I just don’t know how to broach that with the wife… but I do want to win the bet,” he said.