In an effort to win a teenage bet, Kutcher asked Pitt who was married to Aniston at that time if he could take out his wife for a wine and dine.
Ashton Kutcher once asked Brad Pitt if he could take Jennifer Aniston out on a date in a bid to win a teenage bet - but she turned him down. The Hollywood actor had a crush on the former "Friends" star when he was in high school and even saved photographs of her on his computer.
He bet a pal that he would one day wine and dine Aniston - and he couldn't believe his luck when he finally met his dream girl after his career took off. The star was so desperate to land a dinner date with the actress he even asked Pitt, who was married to Aniston at the time, if he would mind letting him take her out.
Kutcher explains to Britain's Graham Norton, "So I make a bet with my buddy. I'm probably 17 years old. I said to him, 'I bet you $1,000 that some day I will go on a date with Jennifer Aniston.' I'm 17 years old and she's like on my screensaver on my computer and he's like. 'You're on...' "
"Four or five years later I actually meet Jennifer Aniston and she's married to Brad Pitt at the time. And so I went to Brad Pitt and I asked his permission to ask his wife out on a date. I said, 'Listen, I made a bet with my buddy, you're a cool guy, you're gonna let this go down, right?' And he looked at me, he's like, 'You go for it.' And I'm like, 'You're the coolest guy I've ever met in my life!' So I asked her and she turned me down... But now we're friends."