Matthew Perry, who’s tragically died at his LA home at the age of 54, enjoyed a series of high-profile relationships during his life, including with some of Hollywood’s most famous leading ladies.

At the height of his Friends stardom in the 90s, Perry romanced Julia Roberts, Neve Campbell and Baywatch star Yasmine Bleeth in the space of just two years.

In later years, his longest romances came via a six-year relationship with actress Lizzie Caplan and an engagement to Molly Hurwitz in 2018, which ended in 2020. 

A month ago, the actor was spotted enjoying lunch in Malibu with a mystery date.

On Saturday, Perry was found unresponsive after an accidental drowning in the jacuzzi of an LA-based home. No drugs were found at the scene and there was no indication of foul play.

 Here, MailOnline looks at the many women linked to Perry during  his life: 

Matthew Perry died on Saturday; the Friends star, who had struggled with an addiction to alcohol and opioids, had many high profile relationships during his life but never married

Julia Roberts: 1995-1996

He dated Julia Roberts for about a year from 1995 to 1996 and how he sabotaged their relationship by ‘dumping’ her before she could leave him

In his memoir Friends, Lovers and the Big Terrible Thing – which was released in November 2022 – he talked about dating Pretty Woman star Julia Roberts.

He said he wooed Roberts with hundreds of fax messages – before ditching her because he feared she would leave him.

Perry revealed that their romance began after the Pretty Woman actress was approached to appear in the sitcom in 1995.

Producers urged him to contact Ms Roberts after she stipulated she would only take a guest role if she could be in a storyline with his character, Chandler Bing.

Perry said: ‘I sent her three dozen red roses and the card 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.”

He revealed that his romance with Julia Roberts began after she was approached to appear in the sitcom in 1995 (pictured)

He also revealed that he sabotaged their relationship by ‘dumping’ her before she could leave him, saying he felt like he could ‘never be enough’ for her.

Perry wrote: ‘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.’

Yasmine Bleeth: 1996 

He had a short romance with Baywatch star Yasmine Bleeth in 1996 who his Friends character, Chandler Bing, had a crush on

Perry had a short romance with Baywatch star Yasmine Bleeth, who his Friends character, Chandler Bing, had a crush on.

After numerous references to the beauty on the sitcom the pair eventually dated in real life. Their short-lived romance took place in 1996, but Chandler continued to make several references to Bleeth in future seasons of the beloved NBC series.

Neve Campbell: 1998

He dated his Three to Tango costar Neve Campbell in 1998. The couple became close while filming but had called it quits before the rom-com even hit theaters

Perry began seeing his Three to Tango co-star Neve Campbell in 1998 while they filmed the movie in Toronto.

However, it was reported that they called it quits before the rom-com even hit cinemas the following year.

Neither Perry nor Campbell have ever publicly addressed this reported relationship.

However, in his memoir, the star did say something rather telling about a romance around this time.

The Friends star dedicated a portion of his book to a former love and the subsequent breakup that ‘still hurts’.

He wrote that this unnamed love made it clear his ‘drinking was a problem.’

He also gave readers a clue about the person’s identity. They met on a film set in 1999 — the same year Perry and Campbell happened to film Three to Tango.

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

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.

Heather Graham: 2003

He also had a brief fling with Cherry star Heather Graham in 2003

Later that year, in 2003 Perry had a rumoured fling with the Scrubs actress Heather Graham. Matthew dated the actress for a couple of weeks and the pair were spotted together several times.

However it was short lived as he soon moved onto another relationship with Gilmore Girls star Lauren Graham.

Lauren Graham: 2003

He was briefly linked to Gilmore Girls star Lauren Graham in 2003 before they called it quits several months later

‘I could not be more single’: Matthew Perry opens up on dating

Perry also found temporary love in actress Lauren Graham in the year 2003.

However the whirlwind romance barely lasted a year, luckily it appeared that there was no bad blood between them, as the former couple went on to work in several movies together after they split.

They both appeared in Studio 60 on the Sunset Strip, NBC sitcom Go On and even played exes on The Odd Couple.

They even appeared in the indie movie Birds of America together in 2008.

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

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 fashion 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 addiction 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)

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

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 October 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 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 dated Molly Hurwitz, who made their relationship Instagram official in February 2020. He proposed to her seven months later

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.

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

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.’

‘You can only held someone so much,’ a close friend of Hurwitz, who was 22 years his junior, told In Touch around the time of their split. ‘He is in a really dark place and pals fear he may have relapsed.

On Saturday, it was reported that Perry was found unresponsive after an accidental drowning in the jacuzzi of an LA-based home.

No drugs were found at the scene and there was no indication of foul play