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Highlights

• Matthew Perry's addiction and substance abuse issues significantly impacted his romantic relationships.
• Perry's breakup with Julia Roberts was influenced by his fear of love.
• Julia Roberts felt embarrassed and uncomfortable with the revelations about their relationship in Perry's memoir.

The legacy of Matthew Perry's beloved character, Chandler Bing, in the hit sitcom Friends, will remain an iconic influence in pop culture. Unfortunately, his tragic passing in October 2023 coincided with the birthday of his former flame and Hollywood luminary, Julia Roberts. Perry and Roberts dated during the mid-1990s, and their relationship blossomed while they worked together on the set of Friends.

Perry became brutally honest about his addiction and substance abuse issues in his memoir Friends, Lovers, and the Big Terrible Thing. His journey through sobriety was marked by constant relapses, which inevitably cast a shadow over his romantic relationships. Despite trying to conquer his fear of love, Perry could not establish a stable relationship and remained unmarried.

Matthew Perry Felt Guilty About His Breakup With Julia Roberts

Matthew Perry and Julia Roberts became close friends before her guest appearance as Susie Moss in the second season of Friends. In his memoir, Perry revealed that Roberts set a condition to let her character be written with Chandler Bing's storyline. After learning Roberts' request, Perry sent her three dozen red roses and a card with his message in it.

Even though Perry and Roberts only dated for a few months, the actor had a chance to meet Roberts' parents during their New Year's trip to New Mexico. Perry talked about his relationship with Roberts and how he ultimately ended it before she had a chance to leave him.

Julia Roberts shared in a 1996 interview on The Late Show With David Letterman that her initial encounter with Matthew Perry was through a phone call rather than a face-to-face meeting. Roberts admitted that she was quite anxious on their first date because Perry is exceptionally witty, humorous, and good-looking.

Perry admitted to his deep infatuation with Roberts, who was already a Hollywood icon then. Despite their undeniable chemistry, he confessed that the pressure of dating Roberts became overwhelming.

He consistently felt a sense of impending breakup from her and believed that Roberts was settling by being in a relationship with him. He reasoned that he was inadequate, unable to measure up, and deemed himself as damaged and unlovable.

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

However, in a resurfaced video, Perry gave a different answer when asked about the reason behind his split from Roberts. The actor clarified that their careers were skyrocketing, and finding time to be together became a challenge, so they amicably decided to part ways.

"... It's like the busiest guy in the world trying to go out with the busiest girl in the world. It just didn't work out, but we are friends and get along really well," Perry explained.

This Is How Much Money Matthew Perry Made From His Poorly-Received Memoir

Matthew Perry's memoir was long-awaited and somewhat poorly received at first, but it still made him a ton of money.

There is no definitive information available to confirm whether Perry ever apologized to Roberts or if she forgave him for their breakup. Their only professional collaboration was on the 1996 episode of Friends titled The One After the Superbowl: Part 2, and they did not share the screen in any other project.

Julia Roberts Did Not Appreciate Matthew Perry's Revelations About Their Relationship In His Memoir

According to reports, Julia Roberts was embarrassed and uncomfortable with Matthew Perry's memoir detailing their romantic relationship. An insider revealed that Roberts felt mortified by the revelations in Perry's book.

"Julia is embarrassed and disappointed that Matthew has detailed their fling. It smacks of Matthew looking for glam soundbites to fill his book and that’s not how Julia rolls," the source revealed.

"She's very old school about her privacy – you never see her kiss and tell about her exes. It made her cringe," the source told Closer Magazine.

Despite Roberts' discomfort at having her private life revealed, she was pleased to witness Perry's journey toward better health and sobriety.

"She knows how badly he struggled and applauds that he’s shown the courage to get help and encourage others to learn from his cautionary tale. Julia just wishes he hadn’t dragged her into his life story," the source stated.

Matthew Perry Was Scared Of Romantic Relationships Because Of His Issues

Matthew Perry delved deeper into his apprehensions about relationships after the publication of his memoir in November 2022. In an interview with People, Perry revealed how his fear of commitment deterred him from marriage and led him to scrutinize his partners for perceived flaws that would lead to resentment.

"That was me afraid. That is what I manifest, something that's wrong with them. And then I break up with them. But there can't be something wrong with everyone. I'm the common denominator. I left first because I thought they were going to annihilate me," Perry explained.

Perry acknowledged grappling with a profound fear of love but also expressed his progress in overcoming it. He emphasized his desire to be with someone who understands the fears that once plagued him.

Matthew Perry's Dating History:

• Jamie Tarses - 1994
• Tricia Fisher
• Julia Roberts - 1995 to 1996
• Yasmine Bleeth - 1996
• Neve Campbell - 1998
• Maeve Quinlan - 2002 to 2003
• Heather Graham - 2003
• Rachel Dunn - 2003 to 2005
• Natasha Wagner
• Lizzy Caplan - 2006 to 2012
• Molly Hurwitz - 2018 to 2021

Perry also shared that during his stay at a rehabilitation facility in Switzerland, he proposed to his then-girlfriend while heavily medicated. "I had even asked for her family's blessing. Then I'd proposed, high as a kite. And on one knee. And she knew it, too. And she said yes," he recalled.

Perry did not name his ex, but he admitted to being taken aback while he pondered on how he ended up in such a situation. He traced the impulsive proposal back to his fear of abandonment and realized that it was driven by desperation to prevent her girlfriend from leaving.

Eventually, Perry realized he wasn't prepared for marriage or commitment. He told his ex his apprehensions and did not even remember the proposal, which ultimately led to their split.

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