Friends star Matthew Perry dated Hollywood’s beautiful women but love eluded him
Matthew Perry dated some of Hollywood’s most beautiful women, but one thing held the star back from finding true love.
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Matthew Perry dated some of the world’s most famous women — and had a long-running crush on co-star Jennifer Aniston— but was stricken with insecurities and feelings of inadequacy.
Hollywood has been left reeling by the death of the Friends star, who was found dead on Sunday in his Los Angeles home at the age of 54.
In his best-selling 2022 memoir, Perry detailed how the childhood trauma of his parents’ divorce and his out-of-control addictions marred his relationships and made it impossible for him to commit.
In Friends, Lovers and the Big Terrible Thing, he revealed he had romanced A-lister Julia Roberts and was falling madly for her.
He then got cold feet and broke up with her due to his fear that he wasn’t good enough for her and she would dump him for being “broken, bent, unlovable”.
Roberts, a huge box office star after the films Pretty Woman and The Player, was a guest star on a 1996 episode of Friends, where she played the character of Susie.
According to Perry, Roberts had said she would only do the guest role if she could have a storyline with Perry’s wisecracking character, Chandler Bing.
Perry wrote, “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.’ ”
Perry ultimately was overcome by fear he would not be enough for the star.
“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,” he confessed.
Perry also had a years-long crush on co-star Jennifer Aniston, who he said kindly reached out to him after the series ended in 2004 to check and see if he was okay.
When he first landed the Friends role, Aniston was the first person he called — although he quickly realised his eagerness had been a mistake.
“I could feel ice forming through the phone,” he wrote. “Looking back, it was clear that this made her think I liked her too much or in the wrong kind of way.”
But instead of leaving it, Perry asked her for a date. “I only compounded the error by then asking her out,” he continued.
“[Jennifer] declined (which made it very difficult to actually go out with her), but said that she’d love to be friends with me, and I compounded the compound by blurting, ‘We can’t be friends!’”
Perry revealed in his book how he would look at Aniston longingly on the Friends set, making their chats “awkward”.
“I’d ask myself, how long can I look at her? Is three seconds too long?”
Perry then became involved with Three to Tango co-star Neve Campbell in 1998 while they were filming but the couple reportedly broke up before the movie came out.
Neither actor publicly addressed the rumoured relationship but in his memoir Perry mentions a relationship that still hurt in which his drinking “was a problem”.
Perry then dated The Bold and the Beautiful actor Maeve Quinlan from 2002 until 2003 and the couple shared a love of tennis. Later that year he was seen with actress Heather Graham and he had a short romance with Gilmore Girls star Lauren Graham.
That relationship only lasted a year although the two actors appear to have ended on good terms, working together in the future on three sitcoms and even playing exes in The Odd Couple.
Perry appears to have next been with British fashion student Rachel Dunn, who was just 19 when they started dating, and Perry was 35.
“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 told the Evening Standard at the time.
The couple broke up not long after Dunn relocated to Los Angeles.
Perry’s longest relationship seems to have been a six year commitment with Fatal Attraction star Lizzy Caplan, ending in 2012. The couple kept the relationship under the radar except for very occasional public appearances, such as when they were spotted at the US Open in New York.
For almost a decade it seemed that Perry wasn’t linked to anyone until literary agent Molly Hurwitz, 22 years his junior, in 2019 when she shared a photo of herself and Perry on Instagram, calling him her “boyfriend” in the post’s caption.
She made their relationship official on Valentine’s Day 2020 by sharing an Instagram post about the actor, saying Perry was her “valentine”. That photo, of Perry asleep on a couch holding a smiley face is the image Perry used as his Instagram avatar until his death.
The couple were engaged but by October 2021, Perry confirmed in a statement they had split up. ”[S]ometimes things just don’t work out and this is one of them. I wish Molly the best,” he said.
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