Ashton Kutcher Tried to Date Jen Aniston for $1,000

February 21, 2011 By:
Ashton Kutcher Tried to Date Jen Aniston for $1,000

Before he became Demi Moore's younger half, Ashton Kutcher made a bet with a friend that he would one day date Jennifer Aniston.

The condition for the $1,000 bet was that Kutcher would go on one date with Jennifer Aniston.

“I was 17 years old and she was on my screensaver," Kutcher said.

Ah, I remember the days Jennifer Aniston was screensaver-worthy. Bellbottoms had finally started fizzling out, and people knew who Robbie Williams was. After Kutcher arrived in Hollywood, he was so intent on making that G, he even got permission from Aniston's then-husband Brad Pitt.

"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," Kutcher said.

You know a man doesn't take you seriously when you ask him permission to ask his wife out and his response is, "go for it". Then again, I guess Brad wasn't terribly concerned on keeping that locked down.

Even though he's happily married, Kutcher hasn't given up hope on that 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.

I know Just Friends didn't get great reviews, but damn, I didn't know Ashton was that strapped for cash. I guess his options at this point are to cash in on old high school bets or shoot another episode of Punk'd.