What Dating Julia Roberts Was Really Like For Matthew Perry

Oh, what could have been! "Friends" fans, do you remember the Season 2 episode, "The One After the Superbowl"? It aired back in 1996 after Super Bowl XXX, and saw the gang hang out on a New York City movie set after Marcel the monkey landed himself a starring role in a movie. You may also remember it for being the "Friends" episode guest starring none other than Julia Roberts as Susie Moss (aka Susie Underpants), who seduced Matthew Perry's Chandler just to leave him in a restaurant bathroom wearing nothing but a pink thong.

Well, it turns out that was all Perry's doing, as he was the one who got her on the show. "Friends" co-creator Kevin Bright confirmed that to The Hollywood Reporter in 2021, sharing, "She wrote back to him, 'Write me a paper on quantum physics and I'll do it.' My understanding is that Matthew went away and wrote a paper and faxed it to her the next day." Writer Alexa Junge then added that the two did a lot of flirting over the medium of fax (have you ever heard anything more 90s than that?), while revealing the whole cast and crew would give him lines to say after Roberts would jokingly ask him why she should go out with him.

And it worked! Yep, Perry and Roberts had a bit of a thing back in the 1990s — but it all got to be too much for the Chandler Bing actor.

Matthew Perry spoke about his 90s romance with Julie Roberts in his book, "Friends, Lovers and the Big Terrible Thing," sharing they were very much a couple when they filmed her "Friends" cameo. "I did let her in, both figuratively and literally, and a relationship began," he recalled (via The Times), revealing he even spent New Year with her family and they rang in 1996 together. But this high-profile romance didn't last long, and the two split after only around two months together. "Dating Julia Roberts had been too much for me. 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, unloveable," he heartbreakingly shared. "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. I can't begin to describe the look of confusion on her face."

Roberts — who divorced Lyle Lovett in 1995 — clearly didn't feel the same way, though. Speaking on "The Late Show with David Letterman" in 1996, she proudly confirmed she was dating Perry and revealed it all started because he called her up out of nowhere. "I was very nervous because he's awfully clever and funny and handsome," she gushed of the actor.