The Friends star dated a string of beautiful women but was ‘afraid’ of love

LONG time bachelor Matthew Perry revealed just a year before his death that he was desperate to settle down and have kids.

In a poignant interview in October 2022, the Friends star revealed he was “not afraid of love anymore”.

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Chandler found happiness with Monica (Courteney Cox) in the show but Matthew Perry never settledCredit: Alpha Press

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Matthew died in his hot tub this weekendCredit: Getty
Tragically, Matthew – who died this weekend at the age of 54 – was never to realise his long-cherished dream of having a family, despite a string of romances with beautiful women throughout his career.

His 27-year battle with drug and alcohol addiction put paid to relationships with the likes of Julia Roberts, Neve Campbell and Yasmine Bleeth, and he was often the one to walk away.

“I manifest something that’s wrong with them, and then I break up with them,” he told People.

“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.”

The Canadian actor, who had 15 different stints in rehab in the 1990s, claimed he was no longer running from love after beating his addiction, in May 2021.

He said: “I’m feeling more confident and I’m not afraid of love anymore, so the next girl I go out with better watch out.”

And he also opened up about his desire to be a dad, saying: “I think I’d be great. I grew up with a lot of little kids around me, and that’s probably why, but I can’t wait.”

Sadly the sitcom legend would never find his ‘lobster’, despite his fame and fortune.

Here we look at the past loves in Perry’s life – and a crippling co-star crush.

Tricia Fisher

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The actor lost his virginity to Tricia FisherCredit: Getty
Perry began dating Fisher – half-sister of late Star Wars legend Carrie – while making his film debut, in A Night in the Life of Jimmy Reardon, at 18.

While the couple fell for each other, Perry initially tried to resist sex.

“My firmness, at least in my conviction to wait, lasted two months… The make-out sessions that didn’t lead anywhere were beginning to cause both of us to hyperventilate,” he wrote in his memoir adding that Tricia eventually made the first move and took him to bed.

While the first attempt failed because “nothing worked” leaving him “soft and sad”, he added that Tricia led him back to bed and, “Sure enough … sheer glory, for two whole minutes!

“That night, by the dint of a miraculous universe and the ministrations of a beautiful young woman who deserved better, I finally first misplaced my virginity then lost it altogether, and impotence has not been part of my vocabulary since, just as she promised it wouldn’t be.”

He added: “Years later, Tricia and I would date again, while Friends was at its peak. She didn’t abandon me, but old fears crept up, and I ended the relationship.”

Gwyneth Paltrow

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He wrote about his ‘closet’ romp with GwynnieCredit: Rex
Although they never officially dated, Perry revealed he and Gwynnie had shared a brief “make-out session in a closet” the summer before Friends hit the screens in 1994.

He later worried the revelation would upset her, telling GQ: “Hopefully, she’ll find it to be a cute story,” he said. “It’d be bad if Gwyneth Paltrow hated me; I wouldn’t like that.”

In a tribute to the star, she called the fling “magical.”

She added: “We drove out to swim in creeks, had beers in the local college bar, kissed in a field of long grass.

“It was a magical summer. He had shot the pilot of Friends but it had not aired yet.

Julia Roberts

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The pair began dating before her appearance on FriendsCredit: Getty
With Friends just a year old, in 1995, Perry’s newfound fame led to his first high profile romance, with Julia Roberts.

The pair became friends, ahead of the Pretty Woman star’s cameo in the second series of the show, after sending “hundreds” of messages every day – by fax.

In his memoir, Friends, Lovers and the Big Terrible Thing, he said: “Three or four times a day I would sit by my fax machine and watch the piece of paper slowly revealing her next missive.”

The pre-text courtship blossomed into romance with their first phone call lasting more than five hours. They went on to date for six months before Perry got cold feet.

“Dating Julia Roberts had been too much for me. I had been constantly certain that she was going to break up with me,” he says. “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.”

Yasmine Bleeth

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Yasmine Bleeth was Chandler’s ideal womanCredit: Rex
Shortly after the split from Roberts, the Friends star moved on to the Baywatch star – named in the sitcom as Chandler’s ideal woman.

As they settle down to watch their favourite Baywatch, Joey teases Chandler about being “in love with Yasmine Bleeth.”

Chandler replies “How can anyone not be in love with Yasmine Bleeth?”

The pair were actually dating at the time – although neither have spoken about it and the romance, in 1996, fizzled out after a few months.

Bleeth never appeared in the sitcom but many think Yasmine may have been “the one that got away” and the character continued to make references to his ex-girlfriend on screen.

Gabrielle Allan

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Gabrielle Allan dated Perry when he was 21Credit: 2011 Getty Images
Veep producer Allan is another ex mentioned in Perry’ autobiography and he says he first realised he was a problem drinker on a night out with her.

“Love of alcohol had indeed become the helmsman of my life, but I don’t think I realised just how much it controlled me until one night when I was out with my girlfriend at the time, Gaby,” he said, adding that they had been to a magic show in University City and returned to her house.

“Gaby didn’t have any alcohol at home, which is, of course, totally fine, but for me at the age of twenty-one, all of a sudden this creeping feeling came over me for the first time,” he said. “I felt my blood on fire for more to drink.”

Jamie Tarses

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Jamie is mentioned in the memoirsCredit: Camera Press
Perry dated Tarses for two years after her divorce from TV producer Dan McDermott, in 1996.

He described her as “the most magical, beautiful, and smart” woman but he ended the relationship because of his struggles.

“I need time to process being sober,” Perry said. “In order to adequately pay sweet Jamie back for two years of giving up huge portions of her own very busy and important life by basically being my nurse, I ended our relationship.”

Neve Campbell 

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The Scream star is thought to have ditched him over drinking
As movies came calling, Perry found himself filming the rom-com Three to Tango in his native Canada, opposite the Scream star in 1999.

The pair reportedly started dating during filming but the relationship ended before the film premiered.

By now, Perry was in the grip of addiction, having become hooked on painkillers following a jet-ski accident in 1997, and had been in and out of rehab.

While neither have spoken about the brief romance, Perry wrote about a mystery woman he met on a 1999 film set, saying she made it clear his “drinking was a problem” and adding that their split “still hurts” to this day.

Maeve Quinlan 

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The two shared a love of tennisCredit: 2002 WireImage.com

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The former lovers together in 2003Credit: 2003 Getty Images
The sitcom star was 33 when he met Quinlan, in 2002.

He dated the Bold and Beautiful star for over a year after bonding over their shared love of tennis.

Again, neither have spilled the beans on their romance, which lasted a year but, in 2003, they were spotted together at a charity tennis event, both with beaming smiles, which suggested they parted on good terms.

Lauren Graham 

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Lauren Graham claimed they flirted but timing was outCredit: Getty
The Gilmore Girls actor was rumoured to have dated Perry in 2003.

They later co-starred in the 2008 movie Birds of America and addressed the “false starts” of their would-be romance,

“I think Lauren and I getting together is largely a timing issue,” Perry admitted.

Graham wrote about flirting with the Friends star in her memoir, Talking as Fast as I Can, revealing they met at an event but it never went further than a flirtation.

She described Perry as her FWIABNED – “Friend Who I Almost But Never Exactly Dated.”

Rachel Dunn

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Rachel was 15 years youngerCredit: PA:Press Association
One of his more serious romances was with fashion student and pro volleyball player Rachel Dunn.

Just 19 when they met, in 2003, Dunn was 14 years his junior and the couple were still together when Friends finally came to an end, in 2004.

Although he has since admitted his crippling addiction meant he didn’t remember filming three series of the sitcom, a stint in rehab in 2001 meant he was sober when he met Dunn.

“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,” he told the Evening Standard in 2004.

“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.”

Marriage seemed to be on the cards when she moved from New York to California but they split in 2005.

“There was no drama, just a commitment by Matthew to stay focused on his sobriety,” a source told People.

His memoir describes her as “The ex-girlfriend of my dreams”.

Lizzy Caplan

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Lizzy was Matthew’s longest relationshipCredit: BackGrid
Perry’s longest relationship was with Mean Girls star Lizzy Caplan, lasting for six years from 2006 to 2012.

The pair met when he gatecrashed her 23rd birthday and, although she is not named in his autobiography, he describes how their romance began as “friends with benefits”.

He also admitted his commitment phobia led to the romance falling apart after they almost got engaged.

He said: “All my fears reared up like a snake.

“I often think if I’d asked, now we’d have two kids and a house. Instead, I’m some schmuck who’s alone in his house at fifty-three.”

Molly Hurwitz

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Molly was the last serious romanceCredit: Instagram/Matthew Perry
The closest the star got to walking down the aisle was with literary manager Molly Hurwitz, who he first met in 2018.

Perry had recently recovered from a near-fatal incident where his colon burst, through opioid abuse, and he was in a coma for two weeks, with his family being told he had a 2 per cent chance of survival.

Hurwitz went public with the romance on Valentine’s Day in 2020, when she posted an Instagram message reading: “Second year being my valentine, but his first as an Instagram influencer. HVD to my favourite.”

She helped support him through his addiction and, in November that year, he revealed he had popped the question.

“I decided to get engaged. Luckily, I happened to be dating the greatest woman on the face of the planet at this time,” he said.

At the time, he was in rehab in Switzerland, where he allegedly lied about pain to get prescription drugs and also suffered a cardiac arrest, with his heart stopping for five minutes.

Six months after announcing the engagement, the pair went their separate ways.

Perry issued a statement saying: “Sometimes things just don’t work out, and this is one of them. I wish Molly the best.”

Jennifer Aniston

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The Friends star had a crush on co-star Jennifer
Friends co-star Jennifer was the huge crush Perry never got over, but she made it clear she had no interest in a romance with him.

The two stars met three years before they were cast in the sitcom – an encounter he recalled in his memoir.

“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.

After landing the role of Chandler, he called Aniston but could sense the attraction was a not mutual

“I could feel ice forming through the phone,” he said.

“Looking back, it was clear that this made her think I liked her too much or in the wrong kind of way.”

He later “compounded the error by then asking her out” but was rejected.

Aniston would later call him out for his drinking – which “saved my life.”

“Imagine how scary a moment that was,” he told TV host Dianne Sawyer. “She was the one who reached out the most. I’m really grateful to her for that.”