I bet a high school buddy $1,000 that one day I would go on a date with Jennifer Aniston. … I was 17 years old and she was on my screensaver. … Five years later I actually met her and I asked Brad Pitt’s permission to ask his wife out on a date. He was so cool and said ‘You go for it’ so I asked her and she turned me down. 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
Ashton Kutcher has a fantasy with about every older woman he knows. During one interview with Graham Norton of the BBC, he confessed that his dream was to date Jennifer Aniston, not Demi Moore.
“I bet a high school buddy $1,000 that one day I would go on a date with Jennifer Aniston”, he said. In the end he took Bruce Willis’ wife on a date. And he ended up with her.