The many women of Matthew Perry’s life

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The many women of Matthew Perry’s life

He rose to fame as the wise-cracking, hopelessly romantic Chandler Bing from Friends, but away from the limelight, Matthew Perry's life was deeply imp

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He rose to fame as the wise-cracking, hopelessly romantic Chandler Bing from Friends, but away from the limelight, Matthew Perry‘s life was deeply impacted by his all-consuming addiction to alcohol and opioids, which affected his ability to find love and settle down. 

The actor, 53, revealed he is looking for a supportive partner to be by his side after overcoming his 30-year-long battle with addiction, and being ‘burned’ by women who were only after his money. 

At the height of his career, Perry, who was universally loved for his role in the 90s classic, found himself an unlikely heartthrob who was linked to some of Hollywood’s most glamourous women.

He dated Julia Roberts for a year from 1995 to 1996, revealing in an extract shared with The Times ahead of the release of his book Friends, Lovers and the Big Terrible Thing, that he sabotaged the relationship by ‘dumping’ her before she could leave him. 

As his addiction to alcohol and opioids took over all aspects of his life, the actor flew from fling to fling, unable to settle with anyone for too long.   

Followed a plethora of short-lived romances with stars including  Neve Campbell, Heather Graham, and Baywatch star Yasmine Bleeth, which led to a controversial two-year relationship with fashion student Rachel Dunn, who was 14 years his junior.  

Perry’s longest relationship was with Mean Girls’ star Lizzy Caplan, which lasted from 2006 to 2012, after which he stayed mainly away from the limelight and was reportedly celibate for nearly half a decade. 

It looked like Matthew had finally found love in 2020, when he proposed to his  girlfriend of two years, the literary agent Molly Hurtwitz, however, the pair called it quits a year later in 2021, with a close pal of the talent manager saying ‘you can only help someone so much. He is in a really dark place and pals fear he may have relapsed,’ In Touch magazine reported. 

JULIA ROBERTS – 1995-1996

Matthew Perry has been linked to several glamourous women throughout his career, but never stayed in the same relationship for too long. In 1995, he dated Julia Roberts, pictured, but revealed to the Times last week he 'dumped' her before she could leave him

Matthew Perry has been linked to several glamourous women throughout his career, but never stayed in the same relationship for too long. In 1995, he dated Julia Roberts, pictured, but revealed to the Times last week he 'dumped' her before she could leave him

Matthew Perry has been linked to several glamourous women throughout his career, but never stayed in the same relationship for too long. In 1995, he dated Julia Roberts, pictured, but revealed to the Times last week he ‘dumped’ her before she could leave him

Perry's latest serious relationship was with literary agent Molly Hurwitz, pictured. The pair got engaged in November 2020, but called it quits in October 2021

Perry's latest serious relationship was with literary agent Molly Hurwitz, pictured. The pair got engaged in November 2020, but called it quits in October 2021

Perry’s latest serious relationship was with literary agent Molly Hurwitz, pictured. The pair got engaged in November 2020, but called it quits in October 2021

The actor’s liaison with Julia Roberts resurfaced last week after he reminisced about their romance in an extract of his upcoming memoirs shared with The Times. 

The Notting Hill lead and Friends’ actor got in touch in 1995, after she was approached to do a celebrity cameo in the Superbowl special episode of Friend’s second series. 

Roberts, Perry revealed, agreed to appear on the show only if she shared a storyline with him. 

He was encouraged by the show’s co-creator Martha Kauffman to send flowers to the actress, something he joked only happens to famous people. 

This led to flirtatious fax exchange between the two actors that last three months before they began dating in earnest.

By the time shooting for the episode started, they were a couple, however, their romance wasn’t meant to last. 

The pressure of dating a Hollywood star like Roberts proved too much to handle for Perry. 

He admitted in his autobiography: ‘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? 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.

‘She might have considered herself slumming it with a TV guy, and TV guy was now breaking up with her. I can’t begin to describe the look of confusion on her face.’

He broke up with the Eat, Pray, Love actress two months after their episode aired, with Roberts moving on to date Miss Congeniality star Benjamin Bratt, with whom she stayed for five years. 

Maeve Quinlan – 2002 – 2003 

From 2002, Perry was linked to The Bold and The Beautiful star Maeve Quinlan. The pair, pictured three years after their breaking up in Bervely Hills, eventually called it quits in 2003

From 2002, Perry was linked to The Bold and The Beautiful star Maeve Quinlan. The pair, pictured three years after their breaking up in Bervely Hills, eventually called it quits in 2003

From 2002, Perry was linked to The Bold and The Beautiful star Maeve Quinlan. The pair, pictured three years after their breaking up in Bervely Hills, eventually called it quits in 2003

The Friends star dating the Bold and the Beautiful blonde for a year, before calling it quits in 2003. 

While she made her debut into the limelight as a professional tennis player, Quinlan rose to fame by playing Megan on the American soap the Bold and the Beautiful, a role she became mainly known for. 

She and Perry became romantically involved in 2002, and were photographed attending several events together, including several caritative occasions. 

In typical Perry fashion, little was known about the relationship, apart from the fact the pair seemed to have a share passion for tennis. 

They eventually split in 2003, but remained on good terms.  

Rachel Dunn – 2003-2005

The actor's most controversial relationship was his two-year love affair with fashion student Rachel Dunn, pictured, who was 14 years younger than him. They dated from 2003 to 2005

The actor's most controversial relationship was his two-year love affair with fashion student Rachel Dunn, pictured, who was 14 years younger than him. They dated from 2003 to 2005

The actor’s most controversial relationship was his two-year love affair with fashion student Rachel Dunn, pictured, who was 14 years younger than him. They dated from 2003 to 2005

After a string of short-lived romances with the likes of Heather Graham, Gilmore Girls’ Lauren Graham or Baywatch babe Yasmine Bleeth, Chandler settled into a relationship with fashion student Rachel Dunn. 

Born in Cambridge, Dunn moved to the US to pursue her fahsion studies and eventually met Perry. 

The couple raised eyebrows, due in large part to the fact that Perry, then 35, was 14 years older than Dunn, who was just 19. 

The pair got together at a time where Perry was clean from his addition to opioids and alcohol. 

Speaking to the Evening Standard in 2004, the actor credited his girlfriend for bringing stability to his life as he recovered from addiction. 

Perry told the Evening Standard in 2004 that Rachel had brought stability to his life and that he was thinking of starting a family with her (pictured at the US Open in 2003)

Perry told the Evening Standard in 2004 that Rachel had brought stability to his life and that he was thinking of starting a family with her (pictured at the US Open in 2003)

Perry told the Evening Standard in 2004 that Rachel had brought stability to his life and that he was thinking of starting a family with her (pictured at the US Open in 2003) 

Eventually, the pair broke up in 2005 after Rachel reportedly moved to the West Coast to be closer to Matthew (pictured in 2004)

Eventually, the pair broke up in 2005 after Rachel reportedly moved to the West Coast to be closer to Matthew (pictured in 2004)

Eventually, the pair broke up in 2005 after Rachel reportedly moved to the West Coast to be closer to Matthew (pictured in 2004) 

He even said the student made him think of settling down and starting a family of his own.  

‘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. 

The affair sparked marriage rumours and Dunn reportedly moved from New York to California to be closer to Perry, however, the romance imploded soon after that. 

At the time of the split, a source close to the couple told People: ‘There was no drama involved (in the breakup), just a commitment by Matthew to stay focused on his sobriety.’ 

Lizzy Caplan – 2006-2012 

The Chandler Bing actor's longest relationship was with Lizzy Caplan, of Mean Girls fame. The couple were so good at keeping their bond under wraps that their breakup only became public a year and a half after thy actually split

The Chandler Bing actor's longest relationship was with Lizzy Caplan, of Mean Girls fame. The couple were so good at keeping their bond under wraps that their breakup only became public a year and a half after thy actually split

The Chandler Bing actor’s longest relationship was with Lizzy Caplan, of Mean Girls fame. The couple were so good at keeping their bond under wraps that their breakup only became public a year and a half after thy actually split  

Perry’s longest relationship was with Mean Girls alum Lizzy Caplan, although very little is known about it. 

Ironically, the affair only became public after the pair called it quits. 

Headlines have often referred to Perry’s love affair with Caplan as a ‘secret relationship,’ due to the fact they stayed largely away from the spotlight, safe from a couple of joint public appearances. 

One of the few times they were seen together was in September 2011 while taking in a US Open tennis match at Flushing Meadows in New York. 

The pair were so discreet that their separation, which took place in 2012, was not made public until a year and a half later in Octboer 2013, with a source telling US Weekly magazine: ‘It happened a year and a half ago,’ the insider says. ‘They haven’t been together for a long time.’ 

At the time, no one knew that the affair p had actually gone on for more than half a decade. 

A source told MailOnline in 2013 that the relationship had been rocky toward the end.

‘For the last year that they were together it was very up and down, a lot of back and forth,’ they said.

 ‘It was hard for them to let go but ultimately Lizzy decided she wanted more.

‘Maybe Matthew just didn’t want to marry Lizzy or maybe he never wants to get married at all,’ adds the source. ‘I don’t know, but I do know it was an issue for them. They’re both decent people. I don’t think the split was ugly.’

Molly Hurwitz – 2018 – 2021 

For three years, Perry date Molly Hurwitz, who made their relationship Instagram official in February 2020. He proposed to her seven months later

For three years, Perry date Molly Hurwitz, who made their relationship Instagram official in February 2020. He proposed to her seven months later

For three years, Perry date Molly Hurwitz, who made their relationship Instagram official in February 2020. He proposed to her seven months later 

The pair eventually split in October 2021, with Perry wishing Hurwitz, pictured, 'the best' in a public statement

The pair eventually split in October 2021, with Perry wishing Hurwitz, pictured, 'the best' in a public statement

The pair eventually split in October 2021, with Perry wishing Hurwitz, pictured, ‘the best’ in a public statement

After nearly seven years where he wasn’t linked to anyone and thought to be celibate, Perry began to date talent manager and literary agent Molly Hurwitz, now 32. 

Reports that the pair were dating began to circulate in late 2019, after they spent the holiday season together in Los Angeles at Perry’s $35million Century City apartment.

At the time, Hurwitz shared a photograph of herself and the Friends star to Instagram, labeling him as her ‘boyfriend’ in the post’s caption.

She wrote: ‘According to my parents’ custody agreement, my mother was not allowed to have a Christmas tree… Fortunately, there’s no such agreement for a daughter’s boyfriend, so Hurwitz gets a treeeeeeee!!!.

The pair became mutually Instagram official in Valentine’s Day 2020, with Molly sharing a sweet post about the actor, hinting it was the second them they were marking the romantic date together. 

‘Second year being my valentine, but his first as an Instagram influencer,’ she wrote. 

Along with the talent manager’s loving words was a photograph of Matthew appearing to be sound asleep, while cradling a bright yellow smiley face balloon which the actor later shared on his own profile. 

Seven months later, Perry told People magazine he had popped the question, dubbing Molly the ‘greatest woman on the face of the planet.’ 

‘I decided to get engaged,’ he told the publication. ‘Luckily, I happened to be dating the greatest woman on the face of the planet at this time.’

Prior to the engagement, rumours circulated that the couple had split in May 2020, but these claims were never confirmed.  

Everyone close to Perry welcomed the news of his engagement at the time. 

A source close to the actor revealed: ‘His inner circle have wanted to see him settle down for a long time, especially Courteney Cox, and they hope him and Molly go the distance.

‘Molly prefers nights in his private cinema watching films and eating home-cooked meals than going out.’

However, the engagement was short-lived, and the actor confirmed to People in October 2021 that the pair had gone their separate ways. 

In a statement, he said: ‘sometimes things just don’t work out and this is one of them. I wish Molly the best.’ 

However, the split happened mere weeks after Perry was outed for using the dating app Raya, where he allegedly asked a 19-year-old girl, ‘Am I as old as your dad?’ during one flirty exchange. 

However, there was no suggestion that the TikTok video exposing the Raya exchange was the reason behind Perry’s split.

A source close to the couple revealed Perry’s struggle with addiction could have been at the source of their separation. 

‘It just wasn’t working anymore,’ they said. ‘You have to hand it to her for hanging in there so long, but you can only help someone so much.’

‘At the end of the day, only Matt can help himself. He is in a really dark place and pals fear he may have relapsed,’ they added. 

Source: | This article originally belongs to Dailymail.co.uk

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