A long time ago, in a galaxy far away, Ashton Kutcher used to be a high school student, and apparently his computer screensaver was rotating photos of his celebrity crush, Jennifer Aniston. Â Ashton bet one of his friends $1,000 that he would one day have a date with Jennifer – and now he intends to win that bet.
It nearly happened once before, back when Jennifer and Brad were still a thing and Ashton was still up-and-coming. Â He asked Brad Pitt for permission to ask Jennifer out, and Brad was totally cool about it and played along. Â Unfortunately, Jennifer turned Ashton down on that occasion, but he says he still holds out hope that one day he’ll win the bet.