Looks like Ashton Kutcher has always been after an older woman…particularly one who happened to be an international celebrity. Apparently while a teen in Iowa, Ashton Kutcher made a bet he would date Jennifer Aniston at some point. Not knowing that Kutcher would one day be the king of Twitter, his friend took the bet of $1,000. We can only imagine the embarrassment one would feel when Ashton Kutcher, millionaire, shows up at your house to collect this month’s rent in payback. Luckily for that guy, Ashton ended up with a different famous cougar. If only he had thought to cover his bases!
Over the next few years, Kutcher proceeded to get Dude, Where’s My Car?-famous, and in his early twenties met Aniston’s then husband Brad Pitt. So he did what any normal megalomaniac would do: he asked Pitt if he could take his wife out for a pizza. “He looked at me and he’s like, ‘You go for it.’ So I asked her and she turned me down,” he laughs. “But now we’re friends.” Ugh, Jen must be kicking herself now, knowing she blew such a golden opportunity. Think about it, girl: that could be your awesome chiseled bikini body getting retweeted by Ashton, rather than your plain old chiseled bikini body getting retweeted by nobody.