Matthew Perry revealed that he broke up with Julia Roberts in the 1990s due to his own mental health issues and feeling of inadequacy. In his new memoir “Friends, Lovers, and the Big Terrible Thing,” the 53-year-old actor opened up about how his struggle with addiction and self-doubt led to the end of their relationship after two months of dating.

Perry said that even though he and 54-year-old Julia Roberts began a romance around the time of her cameo on “Friends,” he was constantly worried she would break up with him. Perry felt that he would "never be enough" for Roberts and that she was “slumming it” by dating him.

Though Perry landed a successful role on “Friends” and Roberts was America's sweetheart, Perry's internal turmoil and fragile self-esteem cut the relationship short, proving that fame and success do not heal underlying personal issues. Yet their brief time together has proven memorable, giving a bittersweet glimpse into what might have been. 

Enlarge ImageMatthew Perry says he broke up with Julia Roberts after feeling like he wasn't good enough for her.FameFlynet / BACKGRID

"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," he confessed.

The "Whole Nine Yards" actor says he can't "begin to describe the look of confusion on her face" after he broke things off.

The pair dated following her guest appearance on "Friends" in Season 2.©Warner Bros/Courtesy Everett C

The pair dated following her guest appearance on "Friends" in Season 2.©Warner Bros/Courtesy Everett C

The whirlwind romance blossomed after Roberts, who went onto wed Danny Moder, claimed she would "only do the show" if she got to be a part of Perry's character's storyline.

After Julia Roberts agreed to appear on “Friends,” Matthew Perry tried to win her over with grand romantic gestures. Perry, who played Chandler Bing, sent Roberts dozens of roses and heartfelt messages, including a paper he wrote on quantum physics. His efforts worked, as Perry said “Not only did Julia agree to do the show, but she also sent me a gift: bagels — lots and lots of bagels. ... I did let her in, both figuratively and literally, and a relationship began.” 

Roberts was clearly charmed by Perry's sweet and quirky attempts at courting her. For a brief time, one of television's most beloved funnymen and America's sweetheart came together, bonding over bagels, roses and quantum physics of all things. Though their relationship did not last, it represented a heartwarming meeting of two major stars on their way up and a story of young love in the dazzle of Hollywood. Sadly, Perry's personal demons would come between them, but the memory of their whirlwind romance lives on as an endearing '90s pop culture moment. 

Matthew Perry struggled with drug and alcohol addiction for decades, even during the height of his fame on Friends. Perry starred as Chandler Bing on the hit NBC sitcom from 1994 to 2004.

However, he went to rehab twice during the show's run, including after filming his character's wedding to Courteney Cox's Monica Geller in the season 7 finale. Perry then went straight from filming to rehab in a pickup truck.Perry said his opioid addiction made it difficult to enjoy being on Friends, despite it being the peak of his career.

His addiction cost him an estimated $9 million to overcome over the years. At the worst of his addiction, Perry was taking 55 Vicodin pills a day, along with methadone, Xanax, and a quart of vodka. Due to the severity of his drug use, Perry nearly died a few years ago when his colon burst, and doctors gave him a 2 percent chance of survival. Though Perry achieved wealth and fame through his role as the funny and likable Chandler Bing, he was battling life-threatening addiction behind the scenes.

His desire to numb his self-doubt and inner turmoil with drugs and alcohol consistently sabotaged his success. Yet through determination and perseverance, Perry survived and learned to value his own well-being over his career and popularity.Now 53, Matthew Perry has come out the other side, newly sober and ready to share his cautionary yet inspiring story of overcoming addiction against all odds.

Though his relationship with Julia Roberts did not last, the memory of their brief time together highlights a turning point before the worst of his struggles, giving a glimpse into the leading man he could have been.

By confronting his demons at last, Perry has a chance to rediscover the gifts within himself that first captivated America -- and Julia Roberts.

His memoir marks the start of a new chapter focused on personal growth rather than chasing fame or lavish gifts. Matthew Perry's story proves that overcoming addiction is a lifelong journey, but one worth fighting for each day.