Matthew Perry's tragic fear that destroyed his love life before drugs spiral

On May 17, 2001, fans all over the world cheered as commitment-phobe Chandler Bing tied the knot with his opposites-attract soulmate, Monica Gellar.

The season seven finale of the wildly popular sitcom ended on a fairytale note. Sadly, as much as he longed for love, Chandler actor who passed away on October 28, 2023, never found his Monica.

Matthew was just 54 years old when he died in the hot tub of his LA home. His , and followed many years of addiction to drugs and alcohol.

Now, Erik Fleming, one of the to 's death, is due to be sentenced. Fleming, 54, pleaded guilty in August to one count of conspiracy to distribute ketamine as well as one count of distribution of ketamine resulting in death. He had initially been due for sentencing on October 30, but this date was ultimately delayed.

At the time of his death, it's believed Matthew had been single and was focusing his efforts on becoming sober. He had, however, been connected to many glamorous women over the years, and had endured a fair few highs and lows in his pursuit of love...

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Jennifer Aniston

From the moment he met her, Matthew admitted he was smitten. "I was immediately taken by her (how could I not be?) and liked her, and I got the sense she was intrigued too - maybe it was going to be something," he wrote in his recent autobiography, Friends, Lovers and the Big Terrible Thing.

And when he landed the Friends gig, Jen was the first person he called - although he quickly realised his eagerness had been a mistake. "I could feel ice forming through the phone," he wrote. "Looking back, it was clear that this made her think I liked her too much or in the wrong kind of way."

But instead of slinking away, embarrassed, Matthew went all in and continued to ask her for a date. "I only compounded the error by then asking her out," he continued. "[Jennifer] declined (which made it very difficult to actually go out with her), but said that she'd love to be friends with me, and I compounded the compound by blurting, 'We can't be friends!'"

The two actors later sat down for their first Friends table read in 1994, and unfortunately for Matt, his feelings continued to linger once filming started, making their conversations 'awkward' as he 'crushed badly' on his co-star. "I'd ask myself, how long can I look at her? Is three seconds too long?"

But by the time Jennifer started dating Brad Pitt in 1998, Matthew said he had "long since gotten over" her and was able to speak to her normally. He said that the success of the show, coupled with her 'deafening lack of interest', eventually cured him and they became lasting friends.

Meanwhile, he also revealed that it was Jennifer who confronted him about his drinking while filming Friends, something he was eternally grateful for, as it forced him to face the situation, a move that undoubtedly saved his life.

The actor, who once , said his co-star asked him outright about his scary drug and alcohol use at the height of his career and praised her for being a good friend. Matthew recalled how Jennifer told him, "We know you're drinking". "Imagine how scary a moment that was," he said. "She was the one who reached out the most, you know. I'm really grateful to her for that."

Julia Roberts

In his autobiography, Matthew revealed how he and Julia Roberts had a three-month relationship. detailed the fiery fling and says it began after was asked to appear as guest character Susie Moss during one episode in 1995.

said he sent Julia 'three dozen red roses' after being told by producers that Julia would take part in the show, only if it involved his character. He said, following a five-hour phone call, Julia turned up at his door and "a relationship began". Just three months later, Matthew says he dumped the Hollywood star over fears he was "certain she was going to break up with [him]".

Failed engagement

Matthew was engaged to literary manager Molly Hurwitz in 2020. Sharing his joy with People magazine, Matthew hailed her as "the greatest woman on the face of the planet." "I decided to get engaged," he said, "Luckily, I happened to be dating the greatest woman on the face of the planet at this time." Sadly, they split just seven months later. In a statement released to People, the Friends star said: "Sometimes things just don't work out, and this is one of them. I wish Molly the best."

Yasmine Bleeth

On the show, Matthew's character, Chandler Bing, was famously a huge fan of Baywatch, and off-screen, he is said to have dated one of the programme's stars, Yasmine Bleeth. According to Page Six, they were together after his fling with Julia in 1996. Two years later, he was linked to his Three to Tango co-star Neve Campbell, while his first serious relationship is said to have been with Bold and Beautiful soap star Maeve Quinlan.

Rachel Dunn

Matthew dated professional volleyball player Rachel Dunn for two years, and they were an item when Friends reached its emotional conclusion in 2004. He made several public appearances with the former fashion student and once told the Evening Standard that she had changed his outlook on life.

"With Rachel in my life, I know that I can be very committed and not some selfish guy who just wants to hang out with friends. I want to spend time with my girlfriend and explore what it means to have a much closer relationship than I've previously had time for," he said.

Lizzy Caplan

Matthew and Mean Girls star Lizzie were together for six years. They started dating in 2006 and flew largely under the radar. But rumours of trouble were rife by 2013 when Lizzie would "not even entertain any questions relating to her partner" during an interview, and covered her ears at the mention of his name.

"I can stand right next to paparazzi, and I do that sometimes. I'm close with people who are far more famous, and they know how to avoid attention," she cryptically said. It later emerged they had split a year earlier.

Why did he never marry?

Matthew once shared the heartbreaking reason he never settled down, admitting he was plagued by intrusive thoughts and fears whenever he was involved with someone. "I break up with them because I'm deathly afraid that they will find out that I'm not enough, that I don't matter, and that I'm too needy, and they'll break up with me," he told GQ magazine ahead of the release of his autobiography.

Determined to stay sober, he explained that he couldn't risk putting his emotions on the line as a split would "annihilate me and I’ll have to take drugs and that will kill me. That's why I break up with these wonderful women that have crossed my path," he added.

Do you have a story to share? Email me at julia.banim@reachplc.com.

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