Matthew Perry's unlucky love life revealed including a broken engagement and fleeting romance with Julia Roberts

WHILE Matthew Perry called off his engagement to Molly Hurwitz this week, it's not the first time he's been unlucky in love.

From Julia Roberts to Lauren Graham and Lizzy Caplan, the 51-year-old has had a string of failed relationships with high-profile women.

Matthew and Julia Roberts hit it off when the actress made a guest appearance on Friends in 1995.

His character Chandler Bing ran into his old school friend Susie [Julia] and they went on a few dates – with Chandler not realizing he'd humiliated her once back in school.

Friends co-creator Kevin Bright claimed that while trying to get Julia to appear on the show, he wrote her an essay on quantum physics.

"She wrote back to him, 'Write me a paper on quantum physics and I'll do it,'" Kevin told The Hollywood Reporter.


"My understanding is that Matthew went away and wrote a paper and faxed it to her the next day."

The costars dated for a year before going their separate ways.

Julia went on to wed camera operator Danny Moder after meeting him on the set of The Mexican in 2000 and they are still together now.

Matthew then moved on to Baywatch babe Yasmine Bleeth – who his character Chandler had a years-long crush on on the show.


The pair dated for several months and have never publicly discussed their romance.

Yasmine, who appeared in 72 episodes of Baywatch, was arrested in 2001 after police found cocaine in her car following a crash

In 1997, Matthew reportedly had a brief fling with her Three To Tango costar Neve Campbell.

But like most Hollywood romances, Neve and Matthew's relationship was over by the time the film hit cinemas.


Matthew dated gorgeous actress Maeve Quinlan from 2002 to 2003.

Things got pretty serious between him and The Bold And The Beautiful star.

Maeve went on to marry Tom Sizemore, but the marriage only lasted three years.

Soon after Maeve, Matthew dated actress Heather Graham and the pair were spotted together several times.


The romance was short-lived and the 17 Again actor soon moved on to Gilmore Girls actress Lauren Graham.

While their relationship was brief, the exes managed to stay friends and even worked together numerous times later on.

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

Matthew and Rachel Dunn looked like they were heading for marriage during their two year romance.

Though he and the former fashion student had a 14-year age gap, they made their relationship work from 2003 until 2005 before calling it quits.

Not long after things ended with Rachel, Matthew then started dating Mean Girls star Lizzy Caplan.

The couple were together for six years but tried to keep their relationship out of the spotlight.

They quietly split in 2012 and sources claimed they broke up because Matthew didn't want to get married.

"He wasn't ready to make the full commitment so they split," an insider alleged to MailOnline at the time.

"For the last year that they were together it was very up and down, a lot of back and forth. It was hard for them to let go but ultimately Lizzy decided she wanted more."

Matthew confirmed this week that his engagement to literary manager Molly, 29, is over.

He told PEOPLE: "Sometimes things just don't work out and this is one of them. I wish Molly the best."

He got engaged to Molly in November 2020 after two years of dating.

However, last week it was reported that Molly put their wedding on hold after he "flirted with other women" while they were on a break.

A 20-year-old recently exposed the actor for flirting with her after they matched on Raya when she was just 19 years old and he was 50.

After his dating app scandal, a source revealed to OK! magazine that Molly wanted to "take a breather".

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