Matthew Perry says he broke up with Julia Roberts because he had low self-esteem and thought he was 'unlovable'

• Matthew Perry spoke about his past relationship with Julia Roberts in his new memoir.

• They began dating in the '90s via fax machine and Roberts guest-starred on an episode of "Friends."

• Perry said he broke up with her because he felt like he was "unlovable" and "could never be enough."

Matthew Perry said that he ended his relationship with Julia Roberts due to his low self-esteem and feelings of unworthiness.

Perry, who starred as Chandler Bing on "Friends," opened up about their romance in his memoir released on Tuesday, titled "Friends, Lovers, and the Big Terrible Thing."

According to the actor, "Friends" cocreator Marta Kauffman suggested he send Roberts flowers because the "Pretty Woman" star was offered a guest spot on season two ("The One After the Superbowl: Part 2") and "she would only do the show if she could be in my storyline."

In his attempt to woo her, they began exchanging messages over fax machines.

"Somewhere in the world, there is a stack of faxes about two feet long — a two-foot-long courtship, filled with poems and flights of fancy and two huge stars falling for each other and connecting in a beautiful, romantic way," Perry wrote in his memoir.

The actor said that Roberts told him she'd agree to appear on the two-part post-Superbowl episode, which aired in January 1996, if he could adequately explain quantum physics to her.

What proceeded was a "three-month-long courtship by daily faxes," according to Perry.

He said that there were "hundreds" of exchanges and "three or four times a day I would sit by my fax machine and watch the piece of paper slowly revealing her next missive."

"They were so smart — the way she strung sentences together, the way she saw the world, the way she articulated her unique thoughts, all was so captivating.," he said. "It wasn't uncommon for me to read these faxes three, four, sometimes five times, grinning at that paper like some kind of moron."

Their romance evolved into hours-long phone calls and they eventually met in person.

By the time Roberts filmed her guest-starring role as Susie Moss, a classmate of Chandler who fooled him into dating her so she could get revenge for a prank he pulled in the fourth grade, the two stars were already dating in real life.

"She was wonderful on the show, and our chemistry seemed to seep off televisions all across America," Perry wrote.

Throughout his memoir, Perry wrote candidly about his addictions, a "lifetime of feeling abandoned," thinking that he's "not enough," and having a "desperate need for love."

His feelings of self-doubt manifested in his relationships, and he broke up with Roberts despite being enamored by her.

"Being on 'Friends' was one of those unicorn situations where the news just kept getting better and better. But off-screen, things weren't going so well," Perry said. "In late April 1996, I went on Jay Leno and admitted I was single. Dating Julia Roberts had been too much for me."

He continued: "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, unlovable. So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts."

Perry said that from his perspective, Roberts was probably caught off guard by his decision.

"She might have considered herself slumming it with a TV guy, and TV guy was now breaking up with her," he said. "I can't begin to describe the look of confusion on her face."

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