From Pretty Women to Nepo Babies, Matthew Perry Dated Some Lovely Ladies

People who struggle with substance abuse also often struggle to hold onto relationships. Be they romantic or platonic, an active addict will often succumb to their disease which leaves little room for much else. Sadly that appeared to be the case for former Friends star Matthew Perry, who struggled with drugs and alcohol most of his life.

He died from a drug overdose in October 2023, alone at his house in Los Angeles. Prior to his death, Matthew wrote a memoir in which he touched on many of the women who passed in and out of his life, each leaving different but significant marks on it. Here's what we know about his dating history.

Matthew talked about dating Tricia Leigh Fisher, half-sister of the late actor Carrie Fisher, in his memoir when he was 18 years old. Their relationship was a slow burn as Matthew waited two months for things to go beyond make-out sessions. She finally made the first move but they split up soon after. The two reconnected years later, but he was too afraid to make a proper go of it.

When it came to dating Julia Roberts, Matthew wrote, "I did let her in, both figuratively and literally, and a relationship began." This was around the time she first guest-starred on Friends, during its second season in 1996. They went on to date a couple of months before Matthew broke things off. "Dating Julia Roberts had been too much for me," he said, noting that he was constantly afraid she would leave him.

Matthew dated future Veep writer/producer when he was 21 years old. This relationship coincided with his first obsessive thoughts about alcohol. In his memoir, he described a time when they went back to her place and Matthew discovered she had nothing to drink. He felt like his blood was on fire.

Jamie Tarses and Matthew started out as pals after meeting in 1994. She was married at the time but after getting divorced in 1996, Jamie and Matthew took their friendship to another level. He described her as magical, beautiful, smart, and said she was by his side during his earlier struggles with substance abuse. After he got sober, Matthew broke up with Jamie so he could figure out how to live his life in this new way. He said he did it as a form of thank you.

From 2003 to 2005, Matthew dated then-fashion student Rachel Dunn. He referred to her as the ex-girlfriend of his dreams and even included her in his will.

Natasha Wagner is the daughter of Natalie Wood and Richard Gregson. Matthew didn't go into too much detail about their relationship, other than the fact that he said they ended things because he didn't date her properly.

Most people know actor Lizzy Caplan from her role as Janis Ian in Mean Girls, or perhaps they caught her hilarious time as a cater waiter in Party Down. What folks probably don't know is that Lizzy dated Matthew for six years. It began as a "friends with benefits" scenario that evolved into dating and an almost engagement. The couple split up in 2012. "I often think if I'd asked [her to marry me], now we'd have two kids and a house," Matthew wrote.

In November 2020, Matthew asked literary manager Molly Hurwitz to marry him. The couple had been dating for two years. They parted ways in June 2021. In a statement to People Magazine, Matthew said, "Sometimes things just don't work out and this is one of them. I wish Molly the best."