Why Matthew Perry & Lizzy Caplan's Relationship Really Fizzled Out

Matthew Perry and Lizzy Caplan carved their own paths in Hollywood. The '90s sitcom "Friends" made Perry one of the most famous names in the world, while Caplan broke out as Janis Ian in the 2004 hit movie "Mean Girls." Many know their filmography very well, but fewer people know their paths actually crossed off-screen. Specifically, it may be surprising to some that Perry and Caplan dated for six years.

Caplan and Perry's relationship was one of his longest public romances. Perry and Caplan began dating in 2006. They were both starring in network shows then: Caplan in "The Class" and Perry in "Studio 60 on the Sunset Strip." TMZ reported that they used to visit each other on their designated sets. However, the relationship blossomed due to the influence of one of Perry's former "Friends" co-stars.

Matt LeBlanc and then-girlfriend Andrea Anders allegedly set them up. Through most of their courtship, Perry and Caplan were a private couple, only appearing together at a few public events. It quietly ended in the 2010s. In Perry's memoir, "Friends, Lovers and the Big Terrible Thing," he gives some insight into how their relationship ended. It started with his fear of proposing. Then, due to his insecurities, their sex life started to disappear. Perry then began to see her as a "best friend only."

Additional relationship problems came from their age differences and stages in their career. Caplan was career-driven at the time, and Perry felt like he retired. At the time of their breakup, in 2012, Caplan was steadily working. Throughout their romance, Caplan actively appeared in TV shows and movies — taking on multiple parts per year. In comparison, Perry appeared in a few projects from 2006-2012. His commitment fear also led to backing out of proposing to her.

In "Friends, Lovers, and the Big Terrible Thing," he details plans to propose to Caplan by giving her a customized painting of them on Christmas. He planned to give her the painting, which included 1,780 hearts (their number of text exchanges at the time), and then ask her to marry him. Perry recalled that his "fears reared up like a snake" and stopped him from asking the big question.

However, he mostly credits his fear of her really seeing him with the end of their romance. "The creeping, nagging, endless fear that if we got any closer, she would see the real me, and leave me. You see, I didn't very much like the real me at the time," shared the "Friends" star. This romance with Caplan was one of Perry's most serious relationships, but not the only one that showcased his commitment issues.

Perry dated a string of famous ladies, including Julia Roberts and Gwyneth Paltrow. However, he never married or had children. Fear kept Perry from making the big commitment leap. In an interview with People, Perry revealed that he often found excuses to end relationships. "That is what I manifest, something that's wrong with them. And then I break up with them," he shared. Perry later understood that he was "the common denominator" and ended things before he could get hurt.

In "Friends, Lovers and the Big Terrible Thing," Perry stated that this fear caused him to break it off with Julia Roberts before it grew deeper. He didn't think he was enough for her. Therefore, he split up with her after only two months together. Though Perry backed out of proposing to Caplan, he did propose to Molly Hurwitz. They eventually called off the engagement.

In 2021, Perry released a statement to People saying things just didn't work out for him and his ex-fiancée. Neither went into details on why their romance ended. However, Hurwitz's Instagram statement after his death showcased some of the complexity of their relationship. A snippet reads, "While I loved him deeper than I could comprehend, he was complicated, and he caused pain like I'd never known."

According to Us Weekly, Caplan and Perry broke up in 2012. However, their breakup didn't become public until 2013. The two were seemingly amicable years afterward until Caplan became engaged. In his memoir, Perry spoke about her emailing him to cut off all communication. He recounted Caplan telling him that "she was getting married and that she had no room in her life for friends." Despite calling her message "harsh," Perry mentioned being glad that she was married and happy.

Caplan started her relationship with her now husband Tom Riley in 2015, a few years after her breakup with Perry. They were engaged in 2016 and married in 2017. Riley and Caplan became parents in 2021. She has often gushed about her husband. In an interview on "Watch What Happens Live with Andy Cohen", Caplan shared how Riley went above and beyond for her 40th birthday. He got people from her life, both past and present, to write about her.

As much as she loves talking about her husband, Caplan doesn't often talk about her relationship with Perry. However, in a Vanity Fair interview from 2022, she revealed that she hadn't read his memoir. She only added, "I have no ill will. I hope the book is really successful."