Matthew Perry Wanted a Family But Never Tied the Knot Despite Dating These Incredible Women

Inside Matthew Perry’s Heartbreaks and Search for Love

Matthew Perry's death shook up Hollywood and his fans all over the world. Even as Perry touched the pinnacles of success and fame, he always felt quite lonely. “I think I’d be great. I really do,” he told PEOPLE in 2022 when it came to having a family. “I grew up with a lot of little kids around me, and that’s probably why, but I can’t wait... 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.” Perry left behind him a trail of broken romances and flings with A-listers such as Julia Roberts, Gwyneth Paltrow, Cameron Diaz, Lizzy Caplan, and Valerie Bertinelli. Here's a closer look at some of his romances and a deep dive into what happened in these relationships.

1. Julia Roberts

Perry's most well-known relationship was with Julia Roberts, whom he dated from late 1995 until early 1996. The Pretty Woman actress agreed to participate in the Super Bowl episode of Friends, but only if she could be a part of Perry's plot. Before they even met or chatted on the phone, this proposal led to a three-month-long courtship by fax between the two, per PageSix. When they first met in person, their romance was steamy and intense. They even rang in 1996 at her Taos, New Mexico, ranch. However, by April, they split up. Perry had dumped America's darling. “Dating Julia Roberts had been too much for me,” Perry admitted in his book. “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.”

2. Valerie Bertinelli

Perry also dated actress Valerie Bertinelli in 1990, when they were both working on the CBS drama Sydney. The only issue? The One Day At A Time actress was married to Eddie van Halen at the time. One night at Bertinelli's place, the two had a protracted make-out session, with Van Halen passing out 10 feet away. According to Perry's book, Bertinelli ignored the hot kiss the next day on the set of Sydney, and Perry got the hint, though he claimed that he was 'devastated.' He even wrote of Bertinelli in his book, stating he was 'obsessed' with the actress: “During filming, I fell madly in love with Valerie Bertinelli. In the early 1990s, there was no one more attractive than Valerie. Not only was she stunning and vivacious, but she also had this great, booming adorable laugh.”

3. Lizzy Caplan

Perry's longest relationship, with actress Lizzy Caplan, lasted from 2006 until 2012. He didn't mention Caplan by name in the book, but he did admit that he almost proposed to the Masters of Sex star but was too terrified, per the New York Post. “I often think if I’d asked, now we’d have two kids and a house with no view…Instead, I’m some shmuck who’s alone in his house at fifty-three, looking down at an unquiet ocean,” he wrote in his book, clearly remorseful of his decision to let her go.

4. Gwyneth Paltrow

Perry also had numerous flings and make-out sessions with renowned women, including Gwyneth Paltrow. Perry detailed making out with her in a broom cupboard at the Williamstown Theater Festival in Massachusetts in 1994 while she was performing in a play there. Paltrow verified the claim in a touching Instagram tribute to Perry after his passing, saying, “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.” Their meeting took place in the summer before Friends had premiered. “We were both still unknown enough that it didn’t make it to the tabloids,” Perry wrote.

5. Cameron Diaz

Among other non-serious partnerships was Perry's tabloid-making 2007 date with Cameron Diaz, which swiftly went off the rails when she was 'immediately stoned' during their group dinner party. Perry unintentionally got smacked in the face by the Charlie's Angels actress while going for his shoulder after saying 'something witty' to the actress during a game of Pictionary, he wrote in his memoir, as per Insider. He explained, "...at one point we were all playing a game — Pictionary, I think. As she was drawing, I said something witty to Cameron, to which she said, 'Oh, come on!' and proceeded to punch me in the shoulder. Or, at least, that's what she meant to do. But she missed and, instead, punched me smack in the side of my face." 

6. Athenna Crosby

Athena Crosby was the most recent woman to go on a date with Perry. The late star was photographed enjoying lunch with the Venezuelan model and entertainment reporter just 24 hours before his untimely death. “He was 100% sober when he passed,” Crosby told Fox News Digital. “I mean, I can’t know what exactly he was thinking or feeling. I can only share my experience. And, of course, he was his own person that maybe he had said, done, or thought of things the day that he passed that I might never come to know.”