Matthew Perry’s Sad, Amazing, Complicated Dating History

Poor Matthew Perry.

The Friends star died so young at just 54 years old, robbing the world of any more brilliant performances. The biggest tragedy, though, was that the lovelorn comic genius never found his one true love.

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But he certainly tried! Perry dated some of the most beautiful and talented women in the world — so many you may even have missed some!

Get the full list of his complicated dating history below…

Gwyneth Paltrow

This was one that really caught us off guard!

Matthew Perry wrote about having a little summer fling with Gwyneth Paltrow in his tell-all, back before they were both huge stars! She revealed more about it in her tribute to him, writing:

“I met Matthew Perry in 1993 at the Williamstown Theater Festival in Massachusetts. We were both there for most of the summer doing plays. He was so funny and so sweet and so much fun to be with. 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.”

Just over a year later he would be a household name on Friends — and so would she soon enough, thanks to roles in films like Seven.

Julia Roberts

Julia was already one of the biggest movie stars in the world when Matthew reached out to her. They had a before-its-time romance, using fax machines back and forth all day to essentially text one another in 1995! After speaking on the phone for the first time — for five hours straight — they knew it was the real deal.

As big a deal as it was in the media, the relationship sadly only lasted about six months. Perry blames himself entirely; he wrote in his memoir, Friends, Lovers and the Big Terrible Thing:

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

Tragically, Perry’s death fell on a day that may haunt Julia — her birthday, October 28.

Yasmine Bleeth

Remember on Friends when Chandler drools over Baywatch babe Yasmine Bleeth? Well, this is how big a cultural impact Friends had immediately — he actually dated her IRL in 1996. Guess she was a fan of the show… and liked what she saw!

It was just a brief fling for Matthew — unlike Chandler, who continued to crush on her for years afterward!

Neve Campbell

Matthew made a pretty underrated gem of a rom com with Neve Campbell in 1998 called Three To Tango. The chemistry apparently extended beyond the screen, with the pair reportedly having an on-set romance. But it didn’t last — by the time the movie came out in 1999, they had already moved on.

It’s also possible she was his “one that got away”…

In his memoir, Matthew refers to a lost love he “never got over.” He doesn’t name her but says she was an actress he met on the set of a movie in 1999. Unfortunately it didn’t work out when she made it clear his “drinking was a problem” and “picked another guy.” He wrote that the breakup “still hurts” — that was over two decades later.

Fans suspect it was Neve because it was the only movie he made that came out that year. It would have filmed in 1998, but it’s assumed he just got the dates a little off. Then again…

René Ashton

For most of 1999, Matthew Perry dated actress René Ashton. They were basically inseparable that whole year!

René seems to be the only other option for that breakup that “still hurts”. He didn’t make a movie with her, but it’s possible he was referring to meeting an actress who wasn’t working on the movie? They were together a long time — and it was while before his next romance…

Maeve Quinlan

Matthew dated soap star Maeve Quinlan from 2002 to 2003. It’s unknown why he and the Bold and the Beautiful actress split, but they seemed to have an amicable breakup as they were seen together years later getting along.

Heather Graham

In 2003, Matthew was rumored to have a brief fling with Heather Graham. Neither he nor the Austin Powers: The Star Who Shagged Me star ever confirmed this, but they were seen together A LOT for a couple weeks. Then she moved on to Edward Burns, and he moved on to…

Lauren Graham

Two Grahams in a row? Well, not exactly. This seemed to be a romantic near-miss for both parties.

Matthew and Lauren Graham met in 2003 and were linked in the media. But were they ever really a couple? The apparently flirted up a storm but just couldn’t get things together! In her own memoir, Talking As Fast As I Can, the Gilmore Girl explains Matthew was her “Friend Who I Almost But Never Exactly Dated” or her “FWIABNED.”

They kept a good friendship, though, even if it never quite materialized into something real. They went on to star in multiple TV and film projects together through the years.

Rachel Dunn

Matthew’s next big relationship was with a young Brit named Rachel Dunn. It was serious enough that, unlike most of his relationships, which he kept very close to the chest, he actually spoke about it publicly! In a 2004 piece in the Evening Standard, he gushed:

“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.”

Perhaps it was the fact she was in his life right at the end of Friends, and he suddenly had enough time to really devote to a personal life? There was even talk of marriage, but it didn’t last. They called it quits in 2005.

Cameron Diaz

We wouldn’t so much say Matthew Perry “dated” Cameron Diaz as he went on A DATE with her. And it did not go well!

In Friends, Lovers and the Big Terrible Thing, Matty revealed he was set up with the Holiday star in 2007, apparently right after her breakup with Justin Timberlake. He got the sense she “wasn’t interested” in the setup at all and that she got “immediately stoned.” Even worse, she hit him!

As he remembers it, he said “something witty” to her during a game of Pictionary, and she went to punch him in the shoulder playfully — and nailed him in the face instead! If you’ve seen the Charlie’s Angels films, you have to imagine that punch HURT! He recalls responding:

“Are you f**king kidding me?”

Like we said, there wasn’t a second date! Hey, sometimes two people might be amazing individually — just not so much together, and they just don’t connect! The next one though…

Lizzy Caplan

This was a big one. THE big one, as it turns out.

Matty was with Lizzy Caplan for about SIX WHOLE YEARS, from around 2007 to 2012! This time Matthew went back to keeping it private — neither gave an interview about it the entire time they were dating OR even after!

But in his book, the Whole Nine Yards star reveals just how close it got. He says he was planning to propose but just never got to it — and she ended up marrying some British guy. (Lizzy married Tom Riley in 2017.) The next time it was that serious, Matthew WOULD propose.

Molly Hurwitz

The last big relationship Perry would ever get the chance for was with a talent manager named Molly Hurwitz. They dated for a couple years starting in 2018, and the sitcom star DID pop the question. The two were engaged about a year before they ended things in 2021.

Neither said much about the relationship of the breakup, with Perry simply saying:

“Sometimes things just don’t work out and this is one of them. I wish Molly the best.”

However, in her social media tribute to her ex after his passing, Molly wrote about how she admired his “brilliance” and had a “magical” time with him. She also said he was “complicated” and caused her a lot of pain. Ultimately we got the idea this was a tough relationship with a troubled artist.

There seems to be some disagreement though, as some of Perry’s friends have come out since to call Hurwitz a “con artist” and to say Matty hated her in the end! Whoa! Maybe not so amicable…

Sadly, though Matthew was said to still be looking for the one right up until his passing, he never did settle down.

[Image via FayesVision/MEGA/WENN/Ben Birchall.]