40 Celebrity Couples You Forgot Dated In The Early ’00s
Ashley Olsen and Lance Armstrong
Lance Armstrong has made some questionable career decisions. No, not only the doping. He also dated Ashley Olsen when he was 36 and she was only 21. His handlers reportedly wanted him to end the relationship because of bad optics, according to the Daily Mail, but the relationship burnt out on its own after a couple of months. Lance moved on to Kate Hudson, and Ashley proved that dating older men wasn’t just a phase. She dated millionaire art dealer Richard Sachs, who is 28 years her elder, Johnny Depp, who is 23 years her senior, and director Bennett Miller, who is 20 years older than her.