Matthew Perry’s Passing on Julia Roberts’ Birthday: A Heartbreaking Connection

After wooing Julia Roberts with three dozen roses and hundreds of faxes, Matthew Perry spent a few months in a love bubble with one of Hollywood’s hottest stars. Persuading her to appear as Chandler Bing’s love interest in a 1996 episode of Friends, the couple shared a palpable chemistry that “seemed to seep off televisions.” But Perry, who was struggling with his insecurities and addictions, said she was “slumming it” with him, and anticipating the “inevitable agony of losing her,” he dumped her.

Breaking her heart one last time, Perry died on October 28, which was also Roberts’ 56th birthday. Following the heartbreaking death of Matthew Perry, sales of his book, “Friends, Lovers and the Big Terrible Thing,” have seen a massive spike. Fans are curious to know more about the beloved star, best known as Chandler Bing on Friends, who was found dead in the jacuzzi of his Los Angeles home.

In his vulnerable memoir, Perry candidly details his relationship with drugs and alcohol, along with the various celebrities he dated over the years. One of those celebrities is superstar Julia Roberts, whom he shared a ’90s romance.

Describing the height of their relationship in 1995, Perry writes, “She was the biggest movie star in the world, and I was on the number one show on TV.” According to his book, Perry and the Pretty Woman star met when Friends co-creator Marta Kauffman asked him to woo her, with flowers and a card, hoping she’d be on an episode of the show.

“(Roberts) would only do the show if she could be in my storyline,” Perry writes. “Was I having a good year or what? But first, I had to woo her.”

Perry accepted the challenge of courting the star of My Best Friend’s Wedding, pleading her to join the cast of Friends for one episode in season two. He explains in his book that he sent three dozen red roses and 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.”

Roberts agreed to be on the 1996 post-Super Bowl episode, but the wooing did not stop there. “Thus began a three-month-long courtship by daily faxes. This was pre-internet, pre-cell phones – all our exchanges were done by fax. And there were many; hundreds,” Matthew writes in his book. “Three or four times a day I would sit by my fax machine and watch the piece of paper slowly revealing her next missive. It was like she was placed on this planet to make the world smile, and now, in particular, me.”

A couple months into their relationship, Roberts appeared on the episode, “The One After the Super Bowl: Part 2.” The Erin Brockovich star played Susie Moss, who was heavily teased by Chandler as a child.

Roberts admitted that she was “nervous” before filming her guest role on the show she called “clever.” “It was utterly nerve-racking,” the Steel Magnolias actress said about sharing the screen with the stars she frequently watched. “They’ve brought me a lot of joy in my life. You feel a little giddy, you feel a little silly. But it was the most fun; it was spectacular fun.”

Meanwhile, Perry expressed his excitement by saying, “She’s an amazing person. She’s everything every guy thinks she is.” In the fan favorite episode, the pair begins seeing one another, and before Susie gets her revenge on her childhood nemesis, the couple shared an on-screen kiss.

“Our kiss on the couch was so real people thought it was real. It was,” Perry says of their intimate moment on the couch in the iconic Central Perk. “She was wonderful on the show, and our chemistry seemed to seep off televisions all across America.”

During their brief romance, the couple even celebrated New Year’s Eve at Roberts’ family home in New Mexico.

Slumming it In this time, the 17 Again star describes his drug and alcohol-induced experiences, like a near-death experience in 2018, a coloscopy bag, temporary erectile dysfunction, and being taken to rehab immediately after he married Monica (Courteney Cox) on Friends.

He also suggests his substance abuse is what led to his breakup with the Oscar-winning actor only two months later.

“‌Dating Julia Roberts had been too much for me. I had been constantly certain that she was going to break up with me. Why would she not?” Perry writes, adding he felt she was “slumming it” with him. “I was not enough; I could never be enough; I was broken, bent, unloveable. So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts.”

On October 28, the comedic genius died, breaking the hearts of millions across the world, including the beautiful Julia Roberts. The Ocean’s Eleven star, who shares three children with her husband of 21 years, celebrated her 56th birthday on the same day.

Despite being notoriously private, Roberts was reportedly “embarrassed and disappointed that Matthew detailed their fling” in his book, and she is likely feeling the heartbreak of losing him again.

Before Perry was found unresponsive in his jacuzzi, he had played pickleball for two hours and then sent his assistant on an errand. When she returned, she found him unresponsive.

Early reports suggest no drugs were found at the scene of Perry’s death, and authorities did not suspect foul play. Law enforcement sources have also told TMZ that a test on Perry revealed he did not have fentanyl or meth in his system at the time of his passing.

The news of his death is still incredibly sad, and it’s hard to believe that Matthew Perry is truly gone. Hollywood has lost one of its brightest stars.