Resident slimeball Ashton “dude lose the trucker hat” Kutcher once tried to beg his way into a date with Jennifer Aniston and even bet a friend $1,000 that he would date her once his career took off.
“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.Four or five years later I actually meet Jennifer Aniston and she’s married to Brad Pitt at the time”. The actor went on, saying, “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.” However, Kutcher revealed that Aniston turned him down on the offer.
You lost! Ha, if his friend was smart he collected interest on that bet. Too bad Ashton didn’t bet him that he wouldn’t sleep with some groupie once he was married to one of the hottest women on earth. Just look at Demi’s face – all the pain behind those glasses and in those lips. She’s on a million-dollar yacht and looks like she needs to puke stat.