Matthew Perry’s dating history: All his girlfriends and relationships

From brief flings with Gwyneth Paltrow and Julia Roberts in the ’90s to a failed engagement with Molly Hurwitz in the 2020s, Matthew Perry dated several women inside and outside Hollywood. The “Friends” star candidly discussed the biggest loves of his life — as well as his struggles with addiction — in his memoir, “Friends, Lovers and the Big Terrible Thing,” which was released one year before his untimely death in October 2023 at the age of 54. Take a look back at everyone Perry was romantically linked to through the years on his quest to find “The One.” Gwyneth Paltrow 1994 Matthew Perry had a summer fling with Gwyneth Paltrow in 1994. Ron Galella Collection via Getty Images In his book, Perry described having a brief “makeout session in a closet” with Gwyneth Paltrow the summer before “Friends” premiered in 1994. The actress later shared that she had met Perry at the Williamstown Theatre Festival in Massachusetts. “We were both there for most of the summer doing plays. He was so funny and so sweet and so much fun to be with. 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. He had shot the pilot of Friends but it had not aired yet. He was nervous, hoping his big break was just around the corner. It was,” she wrote on Instagram. “We stayed friends for a while until we drifted apart, but I was always happy to see him when I did.” Julia Roberts 1995-1996 Perry dated Julia Roberts later in the ’90s. ©Warner Bros/Courtesy Everett C Perry had his first high-profile relationship with none other than Julia Roberts. The sitcom star said he and the “Pretty Woman” star started dating around the time she made a cameo in a 1995 episode of “Friends,” but he broke things off after just two months because he felt like he would “never be enough” for her. “Dating Julia Roberts had been too much for me. I had been constantly certain that she was going to break up with me,” Perry wrote in his book, noting that he felt Roberts was “slumming it” by dating him. Yasmine Bleeth 1996 Perry was later linked to Yasmine Bleeth. Getty Images Sometimes life imitates art: Perry’s “Friends” character, Chandler Bing, had a crush on Yasmine Bleeth following her turn in “Baywatch,” and the pair eventually dated in real life. Their short-lived romance took place in 1996, but Chandler continued to make several references to Bleeth in future seasons of the beloved NBC series. Neve Campbell 1998 Perry also dated Neve Campbell. WireImage Perry made a habit out of dating his co-stars in the ’90s when he began seeing his “Three to Tango” scene partner Neve Campbell. The couple became close while filming the movie in 1998. However, they called it quits before the rom-com even hit cinemas the following year. René Ashton 1999 Perry and René Ashton dated in 1999. WireImage Perry dated actress René Ashton for about a year in 1999. The pair began seeing each other during the height of the actor’s fame on “Friends” and remained together for most of the year. That October, the pair stepped out together publicly at the premiere of the film “Fight Club” in Los Angeles. During their relationship, the “Mother’s Deadly Son” actress said she grew concerned about Perry’s escalating struggle with alcohol — even contacting his father to ask for help. Ashton and Perry called it quits in December 1999. In “The One About Matthew Perry,” the 2026 Netflix three-part documentary doc about Perry’s life, career, addiction struggles and death, Ashton revealed she and the “17 Again” star joined the “mile-high club” on Bruce Willis’ private plane. Maeve Quinlan 2002-2003 The actor had his first serious relationship with Maeve Quinlan. WireImage The “Whole Nine Yards” actor had his first serious relationship with soap star Maeve Quinlan. The “Bold and the Beautiful” alum, who portrayed Megan Conley for over 10 years, was linked to Perry from 2002 to 2003. It’s unclear what caused their split, though fans believe the former couple ended on good terms, as they posed together at a charity event in 2006. Lauren Graham 2003 He briefly dated “Gilmore Girls” star Lauren Graham. WireImage Perry was linked to “Gilmore Girls” star Lauren Graham in 2003, but he was single again just a few months later. It seems there was no bad blood between the pair, as they reunited several times and even appeared in the indie movie “Birds of America” together in 2008. Rachel Dunn 2003-2005 Perry dated Rachel Dunn in the early 2000s. WireImage Perry moved on with professional volleyball player Rachel Dunn in 2003. The athlete made several public appearances with the Emmy nominee and was dating him when “Friends” came to an end. Unlike most of his relationships, which he famously keeps under wraps, Perry spoke publicly about his time with the former fashion student. “With Rachel in my life, I know that I can be very committed and not some selfish guy who just wants to hang out with friends. I want to spend time with my girlfriend and explore what it means to have a much closer relationship than I’ve previously had time for,” he gushed to the Evening Standard in 2004. Lizzy Caplan 2006-2012 Perry’s longest relationship was with actress Lizzy Caplan. SplashNews.com Perry dated “Mean Girls” star Lizzy Caplan for six years, making their romance his longest to date. The Massachusetts-born actor began dating Caplan in 2006, and the two managed to keep their relationship largely out of the spotlight. Read more about Matthew Perry’s life and struggles: 55 Vicodin & a quart of vodka: The most shocking tales from Matthew Perry’s tell-all memoirMatthew Perry: How to tell which drugs I used during ‘Friends’Matthew Perry reveals why he broke up with Julia Roberts in the ’90sMatthew Perry claims Cameron Diaz once punched him in the face on secret dateMatthew Perry, Valerie Bertinelli made out while Eddie Van Halen was passed out Rumors of trouble in paradise first arose in 2013 when the Independent claimed Caplan would “not even entertain any questions relating to her partner” during an interview and even covered her ears when his name was mentioned. “I can stand right next to paparazzi and I do that sometimes. I’m close with people who are far more famous, and they know how to avoid attention,” she told the outlet. It turns out, Perry and the “Masters of Sex” alum had secretly split one year prior. Molly Hurwitz 2018-2020 Perry was engaged to Molly Horowitz. Matthew Perry/Instagram Perry started dating literary manager Molly Hurwitz in 2018. Hurwitz did not confirm their relationship until 2020 when she paid tribute to the “17 Again” star on Valentine’s Day. “Second year being my valentine, but his first as an Instagram influencer. HVD to my favorite,” she captioned an Instagram post. Flash-forward to November of that year, and Perry revealed he had popped the question. “I decided to get engaged. Luckily, I happened to be dating the greatest woman on the face of the planet at this time,” he gushed to People after getting down on bended knee. Six months later, however, the two called off their engagement. “Sometimes things just don’t work out, and this is one of them,” Perry’s rep said in a June 2021 statement. “I wish Molly the best.”