Matthew Perry’s beloved character, Chandler Bing from the hit show Friends, was famous for his romance with Monica Geller (played by Courteney Cox), but what about Perry’s real-life love stories? In his 2022 memoir, Friends, Lovers and The Big Terrible Thing, the late star, who passed away at 54, opened up about his relationships with various high-profile celebrities. Let’s take a trip down memory lane and revisit some of Perry’s memorable romances.
Gwyneth Paltrow, an accomplished actress and entrepreneur, recently shared her reflections on her brief romance with Perry back in 1993. Paltrow reminisced about their “magical summer” and the intimate moments they shared, like kissing in the grass. This happened just before Perry’s breakout role in Friends, which premiered in 1994. According to Paltrow, she met Perry at the Williamstown Theater Festival in Massachusetts, where they both performed in plays. She described him as funny, sweet, and a joy to be around. When they met, Friends had been filmed but not yet aired, and Perry was feeling anxious about his big break. While they eventually grew apart, Paltrow expressed sadness over Perry’s passing and hoped that he had finally found peace.
Perry’s first major Hollywood relationship was with the charismatic actress Julia Roberts. They dated from 1995 to 1996, and their love story began when Friends producers invited Roberts to guest star on the show. However, the pressure of dating such a big celebrity weighed heavily on Perry, and he eventually made the difficult decision to end the relationship. In his memoir, he admitted to feeling certain that Roberts would break up with him, so he decided to break things off first. He described witnessing the confusion on Roberts’ face as he delivered the news.
During the early days of his Friends fame, Perry found romance with Yasmine Bleeth, known for her role in the popular TV series Baywatch. Chandler Bing, Perry’s character on Friends, frequently mentioned his crush on Bleeth throughout the sitcom. Their fling occurred both during and after their time on the show.
Another significant relationship in Perry’s life was with Rachel Dunn, a former fashion student, from 2003 to 2005. In his memoir, Perry referred to Dunn as the ex-girlfriend of his dreams. The couple’s breakup coincided with the end of Friends, but sources close to them emphasized that it was an amicable split. Rather than drama, their separation resulted from Perry’s commitment to maintaining his sobriety.
Lizzy Caplan, known for her role in the acclaimed TV series Masters of Sex, shared a six-year relationship with Perry that ended in 2012. Perry shared in his book that he regretted not proposing to Caplan during their time together. He envisioned a different life for himself, imagining a future with two children and a home. Instead, he found himself alone in his house at 53, pining over missed opportunities.
Perry’s final serious relationship was with literary agent Molly Hurwitz. They began dating in 2018 and announced their engagement in November 2020. Perry expressed his admiration for Hurwitz, calling her the greatest woman on the planet. Unfortunately, the couple called off their engagement in 2021, citing that sometimes things just don’t work out. After Perry’s passing, Hurwitz shared the profound impact that he had on her life. She described him as a complicated person who brought both love and pain into her life, and she expressed deep gratitude for what she had learned from their relationship.
Matthew Perry was not only known for his comedic talents on-screen but also for his intriguing love life off-screen. As we remember this iconic star, we can’t help but wonder about the complexities and mysteries that surrounded his romantic relationships throughout the years.
