Matthew Perry, Age 50 – Single

Matthew Perry has had the chance to play probably one of the most loved characters on television that ever existed, the one of Chandler Bing. As it just so happened, during Friends, he had also had quite a bit of success in his dating life as well, given that he started dating Julia Roberts after she made a guest appearance on the show.

They didn’t last more than a year, however, and Matthew went on to date Lizzy Caplan just two years after the show ended. According to him, their relationship ended after six years because he wasn’t ready to tie the knot. His last appearance was in 2018’s The ‘90s Greatest documentary series.