Matthew Perry — Age 51

Matthew Perry’s Chandler Bing had two notable love interests in Friends: Monica Gellar and Janice Hosenstein. In real life, he only has eyes for one woman, though, and that is Molly Hurwitz. They began dating in 2018, and their romance eventually led to their 2020 engagement.

By playing Chandler on the famous NBC TV series, Perry was reported to be earning $1 million per episode along with his five main co-stars by 2002. Now he’s worth $120 million, as per Celebrity Net Worth. In April 2021, Perry shared a Friends reunion behind-the-scenes snap, but quickly deleted it for some reason.