Matthew Perry was no stranger to high-profile romance.
While the Friends alum would eventually go on to date his fair share of famous celebrities, Perry was vocal about the struggles of maintaining a relationship in the spotlight following the success of his NBC sitcom, in which he starred as Chandler Bing from 1994 to 2004.
Friends, however, did lead Perry to a few big loves throughout his time on the show. In 1995, he began dating Julia Roberts after the Oscar winner made a guest appearance on the comedy series.
Despite their instant chemistry, the pair called it quits just two months into dating, with Perry attributing the split to his insecurities. Following their breakup, Perry entered a few short flings before finding love again with Lizzy Caplan in 2006. They dated for six years before Us Weekly confirmed their split in October 2013.
Five years later, rumors swirled that Perry had sparked a romance with Molly Hurwitz. Us exclusively revealed the pair were dating in January 2020. In November of that same year, Perry confirmed that he had proposed to the talent manager.
Six months after the actor got down on one knee, however, the twosome called it quits.
In October 2023, Perry died at age 54 following an apparent drowning.
Keep scrolling for more of Perry’s dating history over the years: