Who: Emmy-nominated actor Matthew Perry, 53, and Oscar-winning actress Julia Roberts, 54.
How They Met: According to Roberts, her and Perry's first introduction was actually over the phone, not in person. "He called me up...out of the blue," she said during a 1996 interview on The Late Show With David Letterman, after acknowledging that she was "dating this Matthew Perry guy." As for their first date, she added, "I was very nervous because he's awfully clever and funny and handsome."
The pair began dating in 1995 following Julia's guest appearance on Friends as Susie Moss, Chandler Bing's former classmate who came back into his life to seek revenge for a childhood prank that left her humiliated.
Roberts and Perry quickly hit it off, and in January 2021, former Friends writer Jeff Astrof recalled Julia being smitten by Matthew during an interview with The Hollywood Reporter. "I remember standing with her on the sidelines. She kept saying, 'Chandler's so funny!' And I'm like, 'I wrote every one of those lines!'" he shared. "I don't know if she fell in love with Matthew on the spot, but they soon started dating. I felt like Cyrano [de Bergerac]. Like, Chandler is going to date Julia Roberts, and I'm going to go home to my horrible girlfriend. That's my memory of that episode."
Why We Loved Them: Their courtship was old-school and, well..unconventional.
For starters, Perry first asked Roberts to be on Friends via fax, and according to the show's co-creator Kevin Bright, the actress wrote back, "Write me a paper on quantum physics, and I'll do it." Bright added, "My understanding is that Matthew went away and wrote a paper and faxed it to her the next day."
There was apparently a lot of flirting over the fax machine. "She was giving him these questionnaires like, 'Why should I go out with you?' And everyone in the writers' room helped him explain to her why," writer Alexa Junge said. "He could do pretty well without us, but there was no question we were on Team Matthew and trying to make it happen for him."
When They Peaked: On the 1996 Friends episode "The One After the Super Bowl." Their chemistry was undeniable — I mean, just look at them.
The Breakup: With both of their careers skyrocketing at the time, Julia and Matthew had difficulty finding time to see each other, so after about a year of dating, they decided to go their separate ways.
"We saw each other for a time, but basically, that had to end. It's like the busiest guy in the world trying to go out with the busiest girl in the world, Perry explained in an unearthed video from the '90s. "It just didn't work out, but we are friends and get along really well."
Where They Are Now: Since Julia, Perry has been linked to many other A-list actresses over the years — including Neve Campbell, Heather Graham, and Lizzy Kaplan. His most recent relationship was with Molly Hurwitz, a literary manager. The two got engaged in November 2020 but called it off seven months later.
After Friends ended in 2004, Matthew went on to star in movies like 17 Again and Birds of America, but TV was still very much his beat. He guest-starred in shows, such as Scrubs and The Good Wife, and most recently had a leading role as Ted Kennedy in the mini-series The Kennedys After Camelot.
Six years after splitting from Perry, Roberts found her forever with cinematographer Daniel Moder. The two married in 2002, and they share three children together — 17-year-old twins Hazel and Phinnaeus, and Henry, 15.
Roberts's acting career hasn't slowed down since the '90s. Aside from iconic rom-coms (My Best Friend's Wedding, Notting Hill, Runaway Bride), Roberts has also taken on more serious roles, such as Mona Lisa Smile and Erin Brockovich, in which she won an Oscar for Best Actress. And next month, she will appear alongside George Clooney in the romantic comedy Ticket to Paradise.
#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.