Emily Mack
It’s hard to believe that Matthew Perry and Julia Roberts ever dated. But once upon a time in the 1990s, these stars were in puppy love! Coming off a string of successful films — Steel Magnolias, Pretty Woman, Pelican Brief — Roberts was at the top of her game when Perry, of recent Friends fame, asked her out with a dozen roses.
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It was a bold move for Perry, who had just skyrocketed to TV fame the year prior. Even bolder? He’s the one who dumped her.
Matthew Perry and Julia Roberts
Matthew Perry’s new memoir, accurately titled Friends, Lovers, and the Big Terrible Thing, chronicles his year-long battle with addiction amid Friends-mania. As well as a string of high-profile romances. One of these, he reveals, was with Julia Roberts.
Before the A-list Roberts agreed to guest star in Friends‘ post-Super Bowl double episode, the network spent time courting her appearance. And Perry was directly involved in the process. He decided to send Roberts three dozen roses along with a note that 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.”
Could it be any more romantic?
Apparently, it worked. Not only did Roberts appear in the popular episode, as Chandler’s vengeful childhood classmate Susie Moss, but she really fell for Perry! They were officially dating by the time “The One After the Super Bowl” premiered in January of 1996. And in all, they spent three blissful months together.
In the book, Perry writes gushingly over faxing Roberts messages:
“Three or four times a day I would sit by my fax machine and watch the piece of paper slowly revealing her next missive. 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.”
— Matthew Perry in Friends, Lovers, and the Big Terrible Thing
A true ’90s love affair.
As Perry describes it, the entire process left him “grinning like some 15-year-old on his first date.” But it was too good to last. Although he and Roberts talked constantly, he was always wracked with doubt.
“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,” Perry writes, echoing the type of language used to describe his own addiction. And so, he ended things.
“Instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts. She might have considered herself slumming it with a TV guy, and TV guy was now breaking up with her,” he said, adding that: “I can’t begin to describe the look of confusion on her face.”
Poor Matthew. Poor Julia! It was all a case of low self-esteem.
“We were falling; I wasn’t sure into what, but we were falling…”
— Matthew Perry in Friends, Lovers, and the Big Terrible Thing
Roberts is now married to the cinematographer Daniel Moder and they have two children. Perry is still single.
Other Matthew Perry Romances You Forgot About
Throughout Friends, Lovers and the Big, Terrible Thing, Matthew Perry describes many relationships and most of them have one thing in common: Perry was the one to end things. The fear he felt while dating Roberts seems to be a pattern that’s still affecting his life.
Tricia Fisher
As a teen, Perry dated Tricia Fisher, the half-sister of Carrie Fisher and they rekindled their romance years later while Perry was on Friends. He eventually ended things with her.
Gabrielle Allan
In Friends, Lovers and the Big, Terrible Thing, Perry says that it was Allan, the writer and eventual Veep producer, who made him realize he had a problem with alcohol.
Jamie Tarses
Jamie Tarses was a famous network executive, instrumental in the creation of Friends. She dated Perry around the year 2000 and tried to help him get off drugs. But once he was sober, Perry broke up with Tarses, saying he didn’t want her to waste time “basically being my nurse.” Tragically, Tarses died of a stroke in 2021. She was just 56.
Rachel Dunn
Perry dated the young fashion student from 2003 to 2005. At the time of their break up, he told People that he needed to focus on his sobriety.
Lizzy Caplan
Though they kept a low profile, Perry dated the actress Lizzy Caplan for about six years until 2012. That’s when, Perry says, “All my fears reared up like a snake… 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.”
Molly Hurwitz
Perry made headlines when he became engaged to literary agent Molly Hurwitz in 2020. But they split up the following year.
Some More Celebrity Trysts…
Don’t worry, there’s still a bit more juicy content. Although Perry did not technically date these stars, Valerie Bertinelli, Gwenyth Paltrow, and Cameron Diaz all come up in the book.
Perry says that in the early ’90s, he and Bertinelli made out while her then-husband Eddie Van Halen was passed out a few feet away. Prior to Friends, Perry played the younger brother of Bertinelli’s character on the1990 show Sydney.
Perry also revealed that once he and Paltrow made out in a closet in 1994.
Diaz, though, did not hook up with Perry — as far as he’s telling. In the book, Perry says he was set up with the actress in 2007 and describes an awkward date: Diaz “accidentally” hit him in the face.
