Ashton Kutcher & Jennifer Aniston? ‘No Strings Attached’ Star Reveals ‘Friends’ Dating Bet

Ashton Kutcher and Demi Moore may be happily married, but before he hit Hollywood, the actor had his eye on another “Friend-ly” leading lady.

“I bet a high school buddy $1,000 that one day I would go on a date with Jennifer Aniston,” Ashton revealed on “The Graham Norton Show” in an episode which airs next week on BBC America. “I was 17 years old and she was on my screensaver.”

The “No Strings attached” star explained to the Irish comedian that when he finally got to Hollywood and had some success, he turned to Jennifer’s then-husband, Brad Pitt, for some help.

“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.

While he’s now married, Ashton said he still hopes to win his teenage bet.

“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.

As for his life with Demi, Ashton told Graham he was proud that the two have spent nearly a decade together as a couple.

“It’s been eight years which in Hollywood years is about 81 so there’s extra points for that,” he said.

Their relationship, or at least their domestic bliss, didn’t start out very easy. Ashton admitted he was “extremely single” when he met Demi and it took a while for word to get around that he was taken.

“I was living with a buddy who refused to leave when Demi moved in,” Ashton said of his early household moments with his brunette bombshell, whom he eventually married in 2005.

“But it was kind of a good thing,” Ashton added. “It would be the middle of the night and there would be visitors and he would do a lot of intercepting for me! I wanted to keep the relationship private so [I] didn’t put the word out and its pretty hard to slow that train down.”

“The Graham Norton” show airs on Saturdays at 10 PM on BBC America.

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