Ashton Kutcher Wants to Date Jennifer Anniston

Ashton Kutcher once bet a high school friend $1,000 he would go on a date with Jennifer Aniston. The 33-year-old actor — who’s now married to Demi Moore — said he made the bet when he was 17.

Kutcher said he was close to winning the bet when he rose to fame and finally had the chance to meet the 42-year-old Friends star, who was married to Brad Pitt at the time. “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,” Ashton said.

“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.”