Matthew Perry – 51, Actor

His iconic role as Chandler Bing may have considered marriage in the hit sitcom Friends, but actor Matthew Perry has never settled down in real life. He dated several famous stars in the past, including Yasmine Bleeth, Julia Roberts, and Lizzy Caplan. Amidst bringing electricity to our TV screens as a heartthrob, we’ve never seen him walk down the aisle.

In the past years, Perry battled personal issues, so it was expected that he would never settle down. Well, we got it all wrong because he decided to take things to another level when he popped the question to his girlfriend, talent manager Molly Hurwitz, in November 2020. The charming bachelor turned fiancé was happy to share the news of his engagement and told People magazine he is lucky to be dating “the greatest woman.” Their wedding plans aren’t finalized yet, but we hope he will finally have his happily ever after this year.