After years of living in the spotlight, Matthew Perry is coming to terms with his troubled past. The star recently released his latest book, , and details his , including how he ended up and be his healthier self.

The book also details some of his past romantic relationships, including his two-month love affair with Julia Roberts. Decades after their split, Perry confessed to breaking the actress’ heart. The actor also went into detail about why they split up.

Matthew Perry Had To ‘Woo’ Julia Roberts For The Friends Superbowl Episode

At that time, Roberts was already the talk of the town, having starred in films such as

, and .

The team behind was under pressure to do something big after being asked to air right after Super Bowl. They also knew .

“We came up with stories we thought were funny and put it out to our casting to find the best people,” co-creator David Crane explained. “But for this episode, we couldn’t just go with a really good actor. We needed names.”

Ultimately, the name that came up was Roberts. “Getting Julia Roberts was incredibly exciting,” co-creator Marta Kauffman remarked. “We knew she would have the right touch for it.”

And while Roberts seemed to be interested in the idea of doing a episode, the A-list star didn’t necessarily say yes straight away.

For starters, she had certain conditions and . “

Julia had been offered the post-Super Bowl episode in season 2 and she would only do the show if she could be in my story line,” the actor wrote in his memoir, in an excerpt from UK’s . “Let me say that again — she would only do the show if she could be in my story line. (Was I having a good year or what?) But first, I had to woo her.”

So, woo her, Perry did. First, the actor sent her “three dozen red roses” plus a card 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.

'”

In response, Roberts sent Perry “lots and lots of bagels.” The actress also playfully challenged him. “Her reply was that if I adequately explained quantum physics to her, she’d agree to be on the show,” he recalled. “Wow. First of all, I’m in an exchange with the woman for whom lipstick was invented, and now I have to hit the books.”

And as the team behind recalled, Perry took the books seriously. “My understanding is that Matthew went away and wrote a paper and faxed it to her the next day,” executive producer Kevin Bright shared.

The two stars were soon corresponding with each other while Roberts was on a film location in France and that meant communication had to be done via fax.

“Three or four times a day I would sit by my fax machine and watch the piece of paper slowly revealing her next missive…,” Perry wrote.

They Started Dating Before Julia Roberts Did The Friends Episode

By the time Roberts got to the set, she and Perry were already an item. The two had been spending some time together before that with Perry even spending New Year’s with Roberts and her family.

“We jumped in this big blue truck and drove up a mountain, snow swirling around. Eventually we reached a mountaintop, and for a moment the weather cleared, and we could see New Mexico and beyond, all the way back to Canada,” the actor wrote.

“As we sat there, she made me feel like the king of the world. A gentle snow was falling, and with that, 1996 began.”

On set, everyone could also tell that Roberts was smitten. “I remember standing with her on the sidelines,” Jeff Astrof, one of the show’s writers, recalled.

“She kept saying, ‘Chandler’s so funny!’” And while they seemed like the perfect couple, the relationship wouldn’t really last.

Matthew Perry Reveals He Broke Up With Julia Roberts ‘Out Of Sheer Fear’

Even after working on the Super Bowl episode, it almost seemed that Perry and Roberts would end up staying together.

Everything seemed perfect, but Perry was convinced that they weren’t meant to have a happy ending. So, one day, .

“We were driving in a car and being chased by paparazzi and I said, ‘I want to break up with you,’” Perry recalled. “Because I think she fancied herself slumming it with TV Boy. And then TV Boy just broke up with her. And you know that the reason I did that was purely out of fear. I needed to get out.”

After that, Perry recalled Roberts “being upset. And couldn’t believe it.”

Reflecting on their split, Perry has maintained that he is the only one to blame for that heartbreak. “And the reason I broke up with her is out of sheer fear,” he said.

“I was like, She’s going to dump me any minute, so I should probably dump her first. And that was fear-based and probably stupid. But that’s what I did.”

Since then, Perry also revealed that he and Roberts never crossed paths again. “No, I have not run into her. I assume she would be falsely nice. And, you know, I’m sure she’s, of course, moved on,” the actor said.

Perry also made it clear that Roberts had been completely unaware that he was going to talk about their relationship in his book. “But I think she’ll be flattered because I say nothing but wonderful things about her,” he added.