Unlike many Hollywood stars, Matthew Perry kept the details of his love life somewhat under wraps, rarely speaking about his romantic entanglements.
But the Friends actor – who died on October 28, aged 54 – did have his share of high-profile relationships, many of which he spoke about candidly for the first time in his 2022 memoir, Friends, Lovers, and the Big Terrible Thing: A Memoir.
Though Matthew Perry never married, he came close once or twice – but had a habit of ending relationships before they ever progressed to the wedding stage.
"That was me afraid," he told People soon after the memoir's release, of why he was always the one to end relationships.
"That is what I manifest, something that's wrong with them. And then I break up with them," he said.
"But there can’t be something wrong with everyone. I'm the common denominator. I left first because I thought they were going to annihilate me."
He also shared that he "had a tremendous amount of fear" about love for a long time – but it's something he worked hard to overcome.
"Through a lot of work, I've got over that fear," he said.
"I'm going to learn as I go... The next person I really take seriously is somebody that I'm going to be in love with and not be scared by the things that used to scare me."
While many women loved him throughout his lifetime, only one was mentioned in his will.
Former fashion student, Rachel Dunn, dated Perry from 2003 to 2005, and despite their short relationship, the late actor described her as "the ex-girlfriend of his dream" in his memoir.
The two went their separate ways around the same time Friends wrapped up. Now, it has been revealed that Rachel has been listed as a beneficiary of Perry's trust fund, worth over $1 million.
Here's what we know about their relationship and all the other women who made an impact on Perry's life.
Rachel Dunn.
Professional volleyball player Rachel Dunn got together with the actor in 2003, and the pair were dating when Friends came to an end.
"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," Perry told the Evening Standard in 2004.
"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."
The pair were together for two years before calling it quits.
"There was no drama involved [in the breakup], just a commitment by Matthew to stay focused on his sobriety," a source close to the former couple told PEOPLE at the time.
For his part, Perry called Dunn the "ex-girlfriend of his dream" in his memoir.
Tricia Fisher.
When he was 18, Matthew Perry dated Carrie Fisher's half-sister, Tricia – and while he tried to abstain from taking their relationship to a physical level, he wrote in his memoir that they both had a hard time waiting.
"My firmness, at least in my conviction to wait, lasted two months... The make-out sessions that didn't lead anywhere were beginning to cause both of us to hyperventilate," he wrote, adding that Tricia eventually made the move to take things further.
After splitting, the couple reunited several years on, at the height of Perry's Friends success. "Years later, Tricia and I would date again, while Friends was at its peak," he wrote. "She didn't abandon me, but old fears crept up, and I ended the relationship."
Valerie Bertinelli.
In his memoir, Perry shared that he "fell madly in love" with fellow actor Valerie Bertinelli when they starred together as siblings in the early 90s sitcom, Sydney – but while the pair did indulge in one cheeky makeout sesh, it never turned into anything more.
Valerie was, after all, married to rock star Eddie Van Halen. Who happened to be passed out next to them at the time.
"Valerie and I had a long, elaborate make-out session," Matthew wrote in his book.
"It was happening – maybe she felt the same way I did. I told her I had thought about doing that for a long time, and she had said it right back to me."
Gwyneth Paltrow.
Less relationship and more "make-out session in a closet", according to the Friends star, he and the Goop founder hooked up – briefly! – the summer before Friends first hit our screens.
Following Perry's death, Paltrow shared a tribute to social media reflecting on their friendship in the '90s, after meeting in 1993 at a theatre festival in Massachusetts.
"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," she wrote.
"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. We stayed friends for a while until we drifted apart, but I was always happy to see him when I did. I am super sad today, as so many of us are. I hope Matthew is at peace at long last. I really do."
Julia Roberts.
Perry and Roberts first connected after Roberts agreed to appear in Friends' 1995 Super Bowl episode... but only if her storyline involved Perry's character, Chandler Bing.
"I had to woo her," he wrote in his memoir.
"I wanted something a tad flirty. I sent her three dozen red roses, and the card 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'."
Her reply was that if he could explain quantum physics to her, she'd do the show.
"The following day I sent her a paper all about wave-particle duality and entanglement, and only some of it was metaphorical. Not only did Julia agree to do the show, but she also sent me a gift: Bagels – lots and lots of bagels."
For the next few months, the pair sent faxes (yes, faxes!) back and forth, and by the time they were filming the episode in question, they were officially an item.
Perry broke it off eventually, sharing that he thought he "could never be enough" for the movie star.
"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."
Salma Hayek.
Salma Hayek has paid tribute to Perry, her co-star in the 1997 film Fools Rush In, vowing to never forget him.
"There is a special bond that happens when you share dreams with someone, and together you work towards them. I was very moved last year when Matthew shared on his Instagram stories how much he loved Fools Rush In, and how he thought that that film we did together was probably his best movie," she wrote on her Instagram.
"Throughout the years, he and I found ourselves reminiscing about that meaningful time in our lives with a deep sense of nostalgia and gratitude. My friend, you are gone much too soon, but I will continue to cherish your silliness, your perseverance, and your lovely heart. Farewell, sweet Matthew, we will never forget you."
Selma Blair.
After Perry's death, Selma Blair shared a tribute for her "oldest boy friend".
"All of us loved Matthew Perry, and I did especially. Every day. I loved him unconditionally. And he me. And I'm broken. Broken hearted. Sweet dreams Matty. Sweet dreams," she wrote on Instagram, alongside a selfie.
Neve Campbell.
The actors both worked on the late '90s film Three To Tango, and became close during filming. However, things ended between them before the movie was released.
Maeve Quinlan.
Perry and Bold and the Beautiful star Maeve Quinlan dated for around a year. The reason for their split is unknown.
Lizzy Caplan.
According to his memoir, Perry's relationship with Mean Girls actress Lizzy Caplan began as a "friends with benefits" situation – though it would end up being his longest-ever relationship.
The couple dated from 2006 to 2012, though they kept their relationship incredibly private. While he wrote about their breakup in his memoir, Perry doesn't actually name Caplan in the book.
"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 fifty-three," he wrote.
Busy Philipps.
The Cougar Town star opened up about her friendship with Perry on her podcast, Busy Philips is Doing Her Best.
“Finding out about Matt Perry was really hard for me,” she began.
“We’ve known him for a really really long time, we’ve been friends with him, I’ve worked with him on The Odd Couple TV show, [my eldest daughter] Birdie’s godmother [Lizzy Caplan] dated him for a really long time.
"It was just so sad and it feels so weird.”
Molly Hurwitz.
Perry and literary manager Molly Hurwz started dating in 2018 and after two years together, the Friends star asked her to marry him.
"I decided to get engaged," he told PEOPLE at the time. "Luckily, I happened to be dating the greatest woman on the face of the planet at this time."
However, in June 2021, the couple called things off, with Perry sharing in an official statement: "Sometimes things just don't work out and this is one of them. I wish Molly the best."
This article was originally published in October 2023, and has since been updated.
Feature Image: Getty.
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