Matthew Perry and Julia Roberts sent 'flirty faxes' for months. Then there was a knock on his door.

Once upon a time in Hollywood, a handsome, funny sitcom actor slid into the reigning rom-com queen's... fax machine. 

Yep, you read that right. 

Fax machine. 

See, this was a time before mobile phones, dating apps, and Instagram DMs. If you wanted to date someone you had to call them up on their landline. Or in the case of Julia Roberts and the late Matthew Perry, your people had to talk to their people, and then you had to fax each other back and forth for a few months. 

Let me explain. 

In Perry's memior, Friends, Lovers And The Big Terrible Thing, he wrote about his time on Friends, his addiction to opioids, and his relationships with some of the most famous women in Hollywood. One of those women was Roberts, who was one of the most bankable rom-com stars at the time. 

The pair first got in contact with each other when Roberts told producers she would appear on the hit sitcom's 1995 Super Bowl episode, only if her storyline involved Perry's Chandler Bing. 

So the show's co-creator told Bing to get in touch with Roberts and send her flowers. 

Image: Getty. 

“I had to woo her. I wanted something a tad flirty. I sent her three dozen red roses, and the card 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’," he wrote in the book. “Her reply was that if I adequately explained quantum physics to her, she’d agree to be on the show.

“The following day I sent her a paper all about wave-particle duality and entanglement, and only some of it was metaphorical. Not only did Julia agree to do the show, but she also sent me a gift: Bagels — lots and lots of bagels.”

After that exchange, the pair sent each other 'flirty faxes' for three months. 

"This was pre-internet, pre-cell phones. All our exchanges were done by fax," Perry explained in his memoir. 

“And there were hundreds. Three or four times a day I would sit at my fax machine and watch the piece of paper slowly reveal her next missive. Some nights I would find myself out at a 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. Nine times out of 10, one had." 

The Friends star said that after a few months of this back and forth, their feelings for each other deepened. 

“I was grinning like some 15-year-old on his first date. And we had never even spoken yet, much less met each other," he wrote. “Then, early one morning, something changed. Julia’s fax veered on romantic. ‘Call me’, it said, and her phone number was at the bottom.

“Five and a half hours later, as we came to a close, I realised I wasn’t nervous anymore. After that we couldn’t be stopped: We were falling. I wasn’t sure into what, but we were falling." 

That Saturday, Roberts knocked on Perry's door and they met in person for the first time. 

“I let her in, both figuratively and literally, and a relationship began. We would already be a couple by the time we started filming the Friends Super Bowl episode." 

On New Year's in 1996, Roberts flew Perry (in her private jet obviously) to her home in New Mexico to meet her family. 

But just two months later, Perry broke the relationship off. 

Image: Getty. 

“Dating Julia Roberts had been too much for me. I had been constantly certain that she was going to break up with me," he explained. “I could never be enough; I was broken, bent, unlovable. So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts.

“I can’t begin to describe the look of confusion on her face.”

In another part of his memoir, Perry wrote about snogging a young Gwyneth Paltrow in a cupboard, before both of them were household names. 

It was 1994, just before Friends hit our TV scenes, and the pair met at a party in Massachusetts. 

“We slipped off into a broom cupboard and made out," Perry explained in Friends, Lovers And The Big Terrible Thing. 

“This was the last summer of my life when I could make out at a party with a beautiful young woman called Gwyneth and no one, save Gwyneth and I, cared.”

This article was originally published on October 24, 2022 and has been updated.

Image: NBC