Ashton Kutcher has a new interview on UK’s Graham Norton show in which he reveals that he had a bet with a friend in high school for $1,000 that he would score a date with Jennifer Aniston. Apparently that bet had no time limit, because he’s still trying to win it after sixteen years. Does that mean that Demi was his second choice out of the famous women he lusted after during his formative years? As for his relationship with Demi, he says he’s proud of how long they’ve lasted, since “eight years which in Hollywood years is about 81.” Can we interpret that to mean he’s sick of her? Like Aniston, he’s not that skilled at expressing himself so maybe he just meant that they’re solid. He seems kind of perfect for Aniston in a way. He’s got the douche part down.

“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.”

[From Access Hollywood]

After watching the video (above) I think it’s most telling that he prefaced his story about the bet by saying he was 17 when he made it and “I’m living on a farm in the middle of America, [Iowa] really having no chance at having a happy life.” I get it – we don’t want to end up like our parents, but it comes across as callous, like only people in big cities are happy. As far as being offensive it’s very minor, though. It’s not like using the “r” word.

Ashton Kutcher is shown in London on 2/10 (credit: WENN) and with Demi in St. Barts on 2/11. (Credit: Fame) Jennifer Aniston is shown in Berlin on 2/21/11. (Credit: WENN)