Matthew Perry’s Relationship History: Molly Hurwitz, Julia Roberts and More Women the Actor Dated

Valerie Bertinelli

Matthew worked with Valerie Bertinelli on Sydney in 1990, and they shared a kiss off screen as well. The actor opened up about his “long, elaborate make-out session” with Valerie in his memoir.

“It was happening — maybe she felt the same way I did,” Matthew recalled thinking. “I told her I had thought about doing that for a long time, and she had said it right back to me.” He also shared that Valerie’s then-husband, Eddie Van Halen, was sleeping just a few feet away when the kiss happened.

After the book came out, Valerie reacted to Matthew’s confession on TikTok. She posted a video of herself with Taylor Swift singing, “It’s me. Hi. I’m the problem, it’s me,” from her song “Anti-Hero” in the background. Valerie captioned the video, “Anyone misbehave in their 20s and early 30s? Are you mortified?”

Gwyneth Paltrow

Matthew and Gwyneth “briefly” made out in a closet in 1993, which he wrote about in his memoir. Gwyneth also recalled the time they shared together when she paid tribute to the star after his death.

“He was so funny and so sweet and so much fun to be with,” she gushed. “We drove out to swim in creeks, had beers in the local college bar, kissed in a field of long grass. It was a magical summer.” She added, “We stayed friends for a while until we drifted apart, but I was always happy to see him when I did.”

Julia Roberts

Julia appeared on an episode of Friends in early 1996, but her relationship with Matthew began before that. Before Julia landed her role on the sitcom, she told producers that she would guest star if she could be part of Matthew’s character, Chandler Bing’s, storyline. Matthew revealed that he sent Julia flowers when he heard this. The note he included read, “The only thing more exciting than the prospect of you doing the show is that I finally have an excuse to send you flowers.”

They began communicating via fax for three months. “Three or four times a day I would sit by my fax machine and watch the piece of paper slowly revealing her next missive,” Matthew wrote in his book. “I was so excited that some nights I would find myself out at some party sharing a flirtatious exchange with an attractive woman and cut the conversation short so I could race home and see if a new fax had arrived. Nine times out of ten, one had.”

Once Julia’s episode of Friends aired, the two were already dating after spending New Year’s with her family. However, the romance ended after just two months when Matthew pulled the plug on the relationship.

“Dating Julia Roberts had been too much for me,” he admitted. “I had been constantly certain that she was going to break up with me. Why would she not? I was not enough; I could never be enough; I was broken, bent, unlovable. So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts.”

Neve Campbell

Matthew and Neve worked together on Three to Tango in 1998. They briefly dated while filming the movie, but split before it premiered in June 1999.

Maeve Quinlan

Matthew and soap opera star Maeve Quinlan dated for nearly a year in 2002 and 2003, marking his first long term relationship in the public eye. However, the two mostly kept their romance private.

Lauren Graham

Matthew worked with Lauren Graham on a few different projects over the years. The Gilmore Girls star once referred to Matthew as “the friend who I almost but never exactly dated.” She also wrote about their friendship in her memoir, Talking As Fast As I Can, and admitted that they flirted on occasion but never took the relationship further than that.

Jamie Tarses

Matthew met Jamie Tarses in 1994, but they did not start dating until after she divorced her husband two years later. He admitted to being in the throes of his substance abuse issues during the relationship and said that Jamie was there for him through those difficult times.

In the end, Matthew said he ended the romance because he wanted to “process” being sober. “In order to adequately pay sweet Jamie back for two years of giving up huge portions of her own very busy and important life by basically being my nurse, I ended our relationship,” he revealed.

Rachel Dunn

Matthew referred to Rachel Dunn, a professional volleyball player, as “the ex-girlfriend of my dream” in his memoir. The two dated from 2003 until 2005. He was 14 years older than her.

Cameron Diaz

When Cameron split from Justin Timberlake in 2007, she was set up on a date with Matthew. “The date was at a dinner party with a bunch of other people,” Matthew recalled in his memoir. “But upon seeing me, Cameron got almost instantly stoned. It was clear that she wasn’t interested in me at all.

The date ended poorly, too, as Cameron accidentally punched Matthew in the face while the group was playing a board game.

Lizzy Caplan

Matthew and Lizzy Caplan’s relationship began as a “friends with benefits” situation, according to his memoir. They were together for six years before their 2012 split. Matthew admitted that his fear of marriage was part of what led to the split.

“All my fears reared up like a snake,” he wrote. “I often think if I’d asked [her to marry me], now we’d have two kids and a house. Instead, I’m some schmuck who’s alone in his house at 53.”

Molly Hurwitz

Matthew started dating literary agent Molly Hurwitz in 2018. They were together for three years and even got engaged before calling it quits in 2021. Matthew popped the question in November 2020, but the engagement lasted just seven months.

“Sometimes things just don’t work out and this is one of them,” he said after the breakup. “I wish Molly the best.”