Matthew Perry – Age 51 – Actor

Matthew Perry is an American-Canadian actor best known for his portrayal of the unforgettably ironic Chandler Bing, one of the main characters of the hit sitcom Friends. Over the years, he has enjoyed the company of many gorgeous fellow celebs, including Julia Roberts and Lauren Graham, but he never tied the knot.

Come to think of it, his decades-long struggle with addiction may have heavily impacted Perry’s ability to commit to a long-term relationship. However, things are changing for the better in recent years as Perry announced his engagement to current girlfriend talent manager Molly Hurwitz in 2020.