Yet, toward the end of his life, a Hollywood insider with ties to Perry told Page Six, “He didn’t really date. It was sad.

“He was so damaged. For most of his career he was fighting a disease,” said the insider of Perry’s decades-long struggles with drugs and alcohol. “He probably felt like he was incapable of being loved.”

Perry left a string of broken romances and flings with leading ladies like Julia Roberts, Gwyneth Paltrow, Cameron Diaz, Lizzy Caplan, and Valerie Bertinelli.

13“Friends” actor Matthew Perry was eager to have a family of his own, he said before his death on October 28, 2023, but never found the true love he craved.©Warner Bros/Courtesy Everett Co13“I think I’d be great. I really do,” Perry said in 2022 of having a family.Getty Images

In his 2022 memoir, “Friends, Lovers and the Big Terrible Thing: A Memoir,” Perry acknowledged that he often sabotaged these relationships due to his prodigious drug habit, alcoholism, and low self-esteem.

“Even on good days, when I’m sober and I’m looking forward, it’s still with me all the time,” he wrote.

He also blamed his family issues for holding him back in love.

Perry’s mom, Suzanne Morrison, is a former TV anchor in Canada and worked as a press secretary for Prime Minister Pierre Trudeau (the father of current Canadian PM Justin Trudeau).

His father, actor, John Bennett Perry, is best known for Old Spice commercials and stints on shows like “Little House on the Prairie” and “Murder, She Wrote.”

13Perry wrote that he had a crush on Jennifer Aniston before “Friends” hit it big, but she rebuffed him.©Warner Bros/courtesy Everett C

“I have spent my life being attracted to unavailable women,” Perry wrote. “It doesn’t take a psychology degree to figure out that this had something to do with my relationship with my mother.”

One of those unrequited romances was with Jennifer Aniston, who would go on to be one of his co-stars on “Friends.”

Perry met Aniston three years before landing the sitcom, and she turned him down when he asked her out.

According to his book, Aniston said they could be friends.

“I compounded the compound by blurting, ‘We can’t be friends!’” he wrote.

13Perry dumped Julia Roberts because he was afraid she would dump him.FameFlynet / BACKGRID

And while Perry admitted to still being attracted to his co-star when “Friends” started filming in 1994, he wrote that, “we were able to sail right past the past and focus on the fact that we had both gotten the best job Hollywood had to offer.”

A close colleague of Perry’s told Page Six that Aniston, along with their other “Friends” co-stars, is incredibly shaken up over Perry’s death.

“She’s in very bad shape. she’s been in a bad way since the death of her father a year ago, and it’s coming up to the first anniversary [Nov. 11],” the close colleague said.

With “Friends” came success, mega-stardom, and love affairs.

Perry’s most famous pairing was with Roberts, whom he dated from late 1995 to early 1996.

13Perry wrote that he was in love with “Sydney” co-star Valerie Bertinelli and even made out with her — but she was married to Eddie Van Halen and unavailable.Ron Galella Collection via Getty

The “Pretty Woman” star agreed to appear on the Super Bowl edition of “Friends,” but only if she could be part of Perry’s storyline.

That subtle proposition kicked off a three-month-long courtship via fax before they even met or spoke on the phone.

When they did finally connect in person, their romance was hot and heavy.

They even rang in 1996 together at her estate in Taos, New Mexico.

But by April, they were broken up. Perry had dumped America’s sweetheart.

“Dating Julia Roberts had been too much for me,” Perry admitted in his book. “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.”

13Perry dated actress Lizzy Caplan for six years and hinted in his book that he almost proposed to her.SplashNews.com

Another serious coupling was with professional volleyball player and fashion student Rachel Dunn.

The two dated from 2003 to 2005 and made several red-carpet appearances together.

However, despite a two-year relationship, he doesn’t mention Dunn in his tome.

His longest relationship was with actress Lizzy Caplan, which lasted from 2006 to 2012.

Remarkably, he didn’t reference Caplan by name in the book but did confess that he almost proposed to the “Masters of Sex” star — but was too scared.

13Fashion student Rachel Dunn dated Perry for two years but didn’t make it into his memoir.Getty Images

Wrote Perry: “I often think if I’d asked, now we’d have two kids and a house with no view…Instead, I’m some shmuck who’s alone in his house at fifty-three, looking down at an unquiet ocean.”

Although he also didn’t name her in his memoir, the Canadian-born actor discussed “falling hard” for an actress he was working within 1999 — speculated to be Neve Campbell, whom he co-starred in “Three To Tango” with during this time.

According to the book, the woman fell in love with someone else, leaving Perry hurt.

Perry caused a lot of pain himself, especially with the only woman he ever proposed to — Molly Hurwitz, who was 22 years his junior.

Although in his book he doesn’t use the literary agent’s name, he claimed he was so high at the time he didn’t remember the 2020 proposal.

13In his memoir, Perry wrote about “falling hard” for a co-star — speculated to be Neve Campbell — who got away.WireImage

“Wait…how did I get engaged?” he wrote. “There are dogs living in my house. How did this happen?”

The actor confessed: “I bought her a ring because I was desperate that she would leave me. I didn’t want to be this injured and alone during COVID.

“I was high on 1,800 milligrams of hydrocodone when I asked her to marry me … And she knew it, too. And she said yes.”

Hurwitz, who dated Perry from 2018 to 2020, wrote about her ex-fiancé’s death on Instagram: “While I loved him deeper than I could comprehend, he was complicated, and he caused pain like I’d never known. No one in my adult life has had a more profound impact on me than Matthew Langford Perry … ”

13Perry proposed to Molly Hurwitz in 2020, then later wrote he only did it because he was scared of being alone during the COVID-19 pandemic.DIGGZY/JP / SplashNews.com13Hurwitz wrote after Perry’s death that he had caused her “pain like I’d never known.”Instagram/mollyhurwitz

He also had countless make-out sessions and flings with famous women, including Gwyneth Paltrow.

In his book, Perry detailed smooching her in a broom cupboard at the Williamstown Theater Festival in Massachusetts, circa 1994, while she was in a play at the famous theater festival.

Paltrow confirmed the account in her heartfelt tribute to Perry on Instagram last weekend, writing of the summer fling, “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.”

Their rendezvous happened during the summer before “Friends” first aired. “We were both still unknown enough that it didn’t make it to the tabloids,” Perry wrote.

13A 2007 date with Cameron Diaz did not go well for Perry.WireImage

He also canoodled with actress Valerie Bertinelli in 1990 when they were working on a CBS show called “Sydney.” The only problem? The “One Day At A Time” actress was married to rocker Eddie van Halen.

“During filming, I fell madly in love with Valerie Bertinelli,” Perry acknowledged in his book, adding that he was “obsessed” with her. “In the early 1990s, there was no one more attractive than Valerie. Not only was she stunning and vivacious, but she also had this great, booming adorable laugh.”

The two had a long make-out session one night at Bertinelli’s house, with Van Halen passed out 10 feet away.

According to Perry’s book, the next day on the set of “Sydney,” Bertinelli didn’t acknowledge the steamy kiss, and Perry got the hint, though he wrote that he was “devastated.”

The show only aired 13 episodes.

13Perry was seen on a date with model and reporter Athenna Crosby a day before his death.Instagram/kylie_rocket_

The low-key lothario also reportedly dated or had dalliances with Gabrielle Allan, who would become a producer on “Veep” years later; Natasha Wagner, the actress daughter of Natalie Wood; studio executive Jamie Tarses; Heather Graham; Lauren Graham; “Baywatch” babe Yasmine Bleeth; and actress Mandy Moore.

A circa 2007 date with Cameron Diaz quickly went off the rails when she got “immediately stoned” during their group dinner party.

When Perry said “something witty” to the actress during a game of Pictionary, he wrote, that she accidentally hit him in the face while aiming for his shoulder.

The last woman to go on a date with Perry was Athenna Crosby.

The Venezuelan model and entertainment reporter was seen having lunch with the late actor just 24 hours before his shock death.

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13“I have spent my life being attracted to unavailable women,” Perry wrote.Corbis via Getty Images

“He was 100% sober when he passed,” Crosby told Fox News Digital. “I mean, I can’t know what exactly he was thinking or feeling. I can only share my experience. And, of course, he was his own person that maybe he had said, done, or thought of things the day that he passed that I might never come to know.”