Matthew Perry’s Sad, Amazing, Complicated Dating History

Poor Matthew Perry.

The Pals star died so younger at simply 54 years outdated, robbing the world of any extra sensible performances. The largest tragedy, although, was that the lovelorn comedian genius by no means discovered his one real love.

Associated: Stars We Misplaced In 2023

However he definitely tried! Perry dated a few of the most lovely and gifted ladies on this planet — so many it’s possible you’ll even have missed some!

Get the complete listing of his difficult relationship historical past beneath…

Gwyneth Paltrow

This was one that basically caught us off guard!

Matthew Perry wrote about having somewhat summer season fling with Gwyneth Paltrow in his tell-all, again earlier than they had been each big stars! She revealed extra about it in her tribute to him, writing:

“I met Matthew Perry in 1993 on the Williamstown Theater Competition in Massachusetts. We had been each there for a lot of the summer season doing performs. He was so humorous and so candy and a lot enjoyable to be with. We drove out to swim in creeks, had beers within the native faculty bar, kissed in a discipline of lengthy grass. It was a magical summer season.”

Simply over a 12 months later he could be a family identify on Pals — and so would she quickly sufficient, because of roles in movies like Seven.

Julia Roberts

Julia was already one of many greatest film stars on this planet when Matthew reached out to her. They’d a before-its-time romance, utilizing fax machines forwards and backwards all day to primarily textual content each other in 1995! After talking on the telephone for the primary time — for 5 hours straight — they knew it was the true deal.

As large a deal because it was within the media, the connection sadly solely lasted about six months. Perry blames himself solely; he wrote in his memoir, Pals, Lovers and the Massive Horrible Factor:

“Relationship Julia Roberts had been an excessive amount of for me. I had been continuously sure that she was going to interrupt up with me. I used to be not sufficient; I might by no means be sufficient; I used to be damaged, bent, unloveable… So as a substitute of going through the inevitable agony of shedding her, I broke up with the gorgeous and sensible Julia Roberts.”

Tragically, Perry’s dying fell on a day that will hang-out Julia — her birthday, October 28.

Yasmine Bleeth

Keep in mind on Pals when Chandler drools over Baywatch babe Yasmine Bleeth? Nicely, that is how large a cultural impression Pals had instantly — he really dated her IRL in 1996. Guess she was a fan of the present… and appreciated what she noticed!

It was only a transient fling for Matthew — in contrast to Chandler, who continued to crush on her for years afterward!

Neve Campbell

Matthew made a reasonably underrated gem of a rom com with Neve Campbell in 1998 known as Three To Tango. The chemistry apparently prolonged past the display, with the pair reportedly having an on-set romance. But it surely didn’t final — by the point the film got here out in 1999, that they had already moved on.

It’s additionally attainable she was his “one which acquired away”…

In his memoir, Matthew refers to a misplaced love he “by no means acquired over.” He doesn’t identify her however says she was an actress he met on the set of a film in 1999. Sadly it didn’t work out when she made it clear his “consuming was an issue” and “picked one other man.” He wrote that the breakup “nonetheless hurts” — that was over 20 years later.

Followers suspect it was Neve as a result of it was the one film he made that got here out that 12 months. It might have filmed in 1998, however it’s assumed he simply acquired the dates somewhat off. Then once more…

René Ashton

For many of 1999, Matthew Perry dated actress René Ashton. They had been principally inseparable that complete 12 months!

René appears to be the one different choice for that breakup that “nonetheless hurts”. He didn’t make a film along with her, however it’s attainable he was referring to assembly an actress who wasn’t engaged on the film? They had been collectively a very long time — and it was whereas earlier than his subsequent romance…

Maeve Quinlan

Matthew dated cleaning soap star Maeve Quinlan from 2002 to 2003. It’s unknown why he and the Daring and the Lovely actress break up, however they appeared to have an amicable breakup as they had been seen collectively years later getting alongside.

Heather Graham

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

Lauren Graham

Two Grahams in a row? Nicely, not precisely. This appeared to be a romantic near-miss for each events.

Matthew and Lauren Graham met in 2003 and had been linked within the media. However had been they ever actually a pair? The apparently flirted up a storm however simply couldn’t get issues collectively! In her personal memoir, Speaking As Quick As I Can, the Gilmore Woman explains Matthew was her “Pal Who I Virtually However By no means Precisely Dated” or her “FWIABNED.”

They saved a superb friendship, although, even when it by no means fairly materialized into one thing actual. They went on to star in a number of TV and movie initiatives collectively by means of the years.

Rachel Dunn

Matthew’s subsequent large relationship was with a younger Brit named Rachel Dunn. It was critical sufficient that, in contrast to most of his relationships, which he saved very near the chest, he really spoke about it publicly! In a 2004 piece within the Night Commonplace, he gushed:

“With Rachel in my life, I do know that I could be very dedicated and never some egocentric man who simply desires to hang around with pals. I need to spend time with my girlfriend and discover what it means to have a a lot nearer relationship than I’ve beforehand had time for.”

Maybe it was the very fact she was in his life proper on the finish of Pals, and he abruptly had sufficient time to essentially dedicate to a private life? There was even speak of marriage, however it didn’t final. They known as it quits in 2005.

Cameron Diaz

We wouldn’t a lot say Matthew Perry “dated” Cameron Diaz as he went on A DATE along with her. And it didn’t go nicely!

In Pals, Lovers and the Massive Horrible Factor, Matty revealed he was arrange with the Vacation star in 2007, apparently proper after her breakup with Justin Timberlake. He acquired the sense she “wasn’t ” within the setup in any respect and that she acquired “instantly stoned.” Even worse, she hit him!

As he remembers it, he mentioned “one thing witty” to her throughout a recreation of Pictionary, and she or he went to punch him within the shoulder playfully — and nailed him within the face as a substitute! If you happen to’ve seen the Charlie’s Angels movies, you need to think about that punch HURT! He remembers responding:

“Are you f**king kidding me?”

Like we mentioned, there wasn’t a second date! Hey, generally two individuals is likely to be superb individually — simply not a lot collectively, they usually simply don’t join! The subsequent one although…

Lizzy Caplan

This was an enormous one. THE large one, because it seems.

Matty was with Lizzy Caplan for about SIX WHOLE YEARS, from round 2007 to 2012! This time Matthew went again to retaining it non-public — neither gave an interview about it all the time they had been relationship OR even after!

However in his e book, the Complete 9 Yards star reveals simply how shut it acquired. He says he was planning to suggest however simply by no means acquired to it — and she or he ended up marrying some British man. (Lizzy married Tom Riley in 2017.) The subsequent time it was that critical, Matthew WOULD suggest.

Molly Hurwitz

The final large relationship Perry would ever get the prospect for was with a expertise supervisor named Molly Hurwitz. They dated for a pair years beginning in 2018, and the sitcom star DID pop the query. The 2 had been engaged a couple of 12 months earlier than they ended issues in 2021.

Neither mentioned a lot in regards to the relationship of the breakup, with Perry merely saying:

“Typically issues simply don’t work out and that is certainly one of them. I want Molly one of the best.”

Nevertheless, 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 additionally mentioned he was “difficult” and brought on her a variety of ache. In the end we acquired the thought this was a tricky relationship with a troubled artist.

There appears to be some disagreement although, as a few of Perry’s pals have come out since to name Hurwitz a “con artist” and to say Matty hated her in the long run! Whoa! Possibly not so amicable…

Sadly, although Matthew was mentioned to nonetheless be searching for the one proper up till his passing, he by no means did quiet down.

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