When Julia Roberts and Matthew Perry Sent 'Flirty Faxes' and More During Their 'Friends' Courtship

Julia Roberts and the late actor Matthew Perry's romantic relationship was the talk of the town in the 90s. It all started with some flirty faxes between them. Perry was a regular cast member on Friends. Roberts was going to be a guest star in one episode. The Friends creators really wanted Roberts to appear on the show. They knew she'd be perfect for the role. Perry took matters into his own hands to get Roberts on board. When he asked her to do the episode, Roberts said she'd only agree if Perry wrote her a paper on quantum physics.

Perry went ahead and wrote the paper. He faxed it to Roberts the very next day. Talk about going the extra mile! But the flirty faxes just started from there. Roberts later started sending Perry little questionnaires asking why she should date him. The whole Friends writers' room helped Perry craft his responses to Roberts's questions. One writer of the show said they were totally "Team Matthew" and trying their best to make things happen between him and Julia, as per Grazia Magazine. Another writer joked that even though he wrote all of Chandler's funny lines, Roberts just kept saying how funny Perry was when filming.

After all the faxing back and forth, Roberts and Perry did end up dating for a while in the mid-90s. However, they kept their relationship pretty private. Roberts later mentioned she was initially intimidated by how clever, funny, and handsome Perry was when he first approached her about being on Friends. Unfortunately, the relationship didn't last. Roberts went on to marry her current husband, Danny Moder, in 2002. 

In his biography Friends, Lovers, and the Big Terrible Thing, Perry, according to Page Six, he provided some insight into the circumstances surrounding the breakup of his relationship with Roberts. According to Perry, he frequently thought that he wasn't "enough" for her. In addition, he said that their falling out was caused by his ongoing sense of being "not enough." Perry described himself as "broken, bent, unlovable" in a depressing piece. "Instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts," he wrote in his book.

The late actor talked more nostalgically about his relationship with the highly regarded actress at the time, showing considerable vulnerability in the process. As stated in the previously cited memoir, "Dating Julia Roberts had been too much for me. I had been constantly certain that she was going to break up with me." Furthermore, Perry said that because Roberts was seeing him romantically, she was "slumming it."