This article was originally published on WHerMoments
The world was shocked when beloved Friends star Matthew Perry passed away in October 2023 aged 54. Less than a year earlier, he’d published his autobiography, Friends, Lovers, and the Big Terrible Thing. That “terrible thing” was his struggles with addiction; he confessed to relapsing “60 or 70 times” during his lifetime at the cost of nearly $9 million. Regardless, his fans, family, and co-stars loved him — as proved by the glowing tributes that poured in after his death. In his book, Perry also opened up about his love for his co-stars and admitted that his feelings for them went a lot deeper than people thought.
Mixing business with pleasure
Perry’s dating history is pretty fascinating. In 1995, for instance, the actor began dating possibly the most sought-after actress of the time: Julia Roberts.
The Pretty Woman star famously played Chandler Bing’s girlfriend in the 1996 Friends two-parter, “The One After the Superbowl.” “Dating Julia Roberts had been too much for me,” Perry wrote in his book. “I had been constantly certain that she was going to break up with me.”
Driven by fear
The Friends star also revealed that he thought Roberts was “slumming it” and that she would soon dump him. “Why would she not?” he asked.
“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 added that he couldn’t “begin to describe the look of confusion on her face” when he did it.
Not pulling any punches
It's clear, then, that Perry put it all on the table in this memoir. “So much has been written about me in the past,” the actor reasoned with People during the promo tour in October 2022, almost exactly a year before he died.
“I thought it was time people heard from me. The highs were high, the lows were low. But I have lived to tell the tale, even though at times it looked like I wouldn’t. And it’s all in here.” That includes his secret dating history, his feelings for his Friends co-stars, and his addiction journey.
Co-stars show their support
Some of the information was even new to his Friends friends. Lisa Kudrow expressed this in the forward to Perry’s memoir.
“[Perry] has survived impossible odds, but I had no idea how many times he almost didn’t make it,” Kudrow wrote. She explained how this was the first time she’d understood Perry’s journey “in detail” as well. “He’s now letting us into Matthew’s head and heart,” she added.
Alarming details
So while fans may have already heard about Perry’s struggles with addiction, they’d never seen them laid out quite like this. “I have spent upward of $7 million trying to get sober,” the actor wrote in the opening pages of the book (he later told the New York Times that it was closer to $9 million).
“I have been to six thousand AA meetings… I’ve been to rehab 15 times. I’ve been in a mental institution, gone to therapy twice a week for 30 years.…”
Shedding new light on Friends
The actor even revealed that his time on everybody’s favorite sitcom was particularly troubled. “My weight varied between 128 pounds and 225 pounds during the years of Friends,” Perry admitted.
“You can track the trajectory of my addiction if you gauge my weight from season to season — when I’m carrying weight, it’s alcohol; when I’m skinny, it’s pills. When I have a goatee, it’s lots of pills.”
An accident and an addiction
The pills thing actually started during a break in filming Friends. Perry had an accident on a Jet Ski around Lake Mead, and a doctor later prescribed a pill to make him feel better.
“As the pill kicked in, something clicked in me,” Perry wrote in his memoir. “And it’s been that click I’ve been chasing the rest of my life.” But his addictions didn't go unnoticed by his castmates.
An open secret
“Everybody knew,” Perry told GQ in October 2022. “The cast of Friends knew.
Jennifer Aniston took me aside once and said, ‘We know you’re drinking.’ And I said, ‘How do you know?’ And she said, ‘We can smell it.’ And that didn’t stop me.” He elaborated on this — and how Aniston had looked out for him — in an interview with Diane Sawyer.
An intervention
"I thought I was hiding it so well," Perry told Sawyer in the October 2020 interview on ABC. "But I wasn't in a position to stop." So when Aniston stepped in to help him, he was appreciative.
"Imagine how scary a moment that was," he said. "She was the one that reached out the most, and I’m really grateful to her for that." The book also detailed Perry’s deeper feelings for Aniston.
A secret crush
The actor revealed that he’d actually met Aniston before they were cast in Friends together. He wrote, “I was immediately taken by her (how could I not be?) and liked her, and I got the sense she was intrigued too — maybe it was going to be something.”
So when he got cast in the sitcom, he decided to give her a call.
An icy reception
He reasoned that Aniston was “the first person [he] wanted to tell this to.” But he quickly found out that this was a “bad idea.”
Perry said he could “feel ice forming through the phone” during his call to her. “Looking back, it was clear that this made her think I liked her too much or in the wrong kind of way,” he wrote, “and I only compounded the error by then asking her out.”
A no-go
“She declined (which made it very difficult to actually go out with her),” Perry admitted, “but said that she’d love to be friends with me, and I compounded the compound by blurting, ‘We can’t be friends!’” Despite this awkward phone call, though, the feelings Perry had for Aniston refused to go away.
And this was even after they started working together.
A major crush
“Fairly early in the making of Friends, I realized that I was still crushing badly on Jennifer Aniston,” Perry wrote. “Our hellos and goodbyes became awkward.
And then I’d ask myself, how long can I look at her? Is 3 seconds too long?” But it didn’t last forever. The actor admitted, “That shadow disappeared in the hot glow of the show. (That, and her deafening lack of interest.)”
Set up with Cameron Diaz
We know, of course, that Perry later hooked up with Julia Roberts. But he also revealed in his memoir that he once had a secret date with another A-lister: Cameron Diaz.
He explained that he was set up with Diaz not long after she had broken up with Justin Timberlake. But according to the Friends star, the date did not go well.
A punch to remember
Perry wrote in Friends, Lovers, and the Big Terrible Thing that Diaz got “immediately stoned” while at a group dinner with Perry. He also said that she “wasn’t interested in [him] at all.”
But the worst was yet to come. Perry revealed that he had said “something witty” to Diaz and then she had “accidentally” struck him in the face while trying to punch his shoulder. “Are you kidding me?” was Perry's reply at the time. So it’s safe to assume there was no second date.
No hard feelings
But Perry told Good Morning America that he was not trying to hurt anybody’s feelings by including these stories in his book. “It’s very important to me that I didn’t go after anyone, and I wasn’t gossipy,” he said.
Yet even though he told GQ that his Friends co-stars are “not going to really care about” the book, he did end up upsetting someone.
Too close to a co-star
In one part of Perry’s book, he revealed that he’d had a crush on Valerie Bertinelli. The pair were filming the short-lived 1990 TV series Sydney at the time — and Bertinelli was married to Eddie Van Halen.
But Perry said that the union was “troubled” and that he had “elaborate fantasies about her leaving Eddie Van Halen and living out the rest of her days” with him.
Making out
Then, on one memorable occasion, Eddie Van Halen — according to Perry — “enjoyed the fruits of the vine a little too hard” and “passed out not 10 feet away” from Perry and Bertinelli. The actor revealed that he and his Sydney co-star then had “a long, elaborate make-out session.”
But while this may have been a dream come true for the young actor, it soon turned into a nightmare.
A bad ending
“I told her I had thought about doing that for a long time, and she had said it right back to me,” Perry wrote in his memoir. But if he thought they were going to live happily ever after, he had another thing coming.
The Friends star admitted that Bertinelli “made no mention of what had happened” after that one night — leaving Perry “devastated.” Yet Bertinelli was seemingly less than happy with being name-checked in the book.
Mortified
The actress — who is now 62 years old — replied via a video on TikTok video. She captioned it, “Anyone else misbehave in their 20s and early 30s?
Are you mortified?” But, of course, what everybody really wants to know is how Jennifer Aniston, Lisa Kudrow, and Courteney Cox feel about the things Perry wrote and said about them.
Serial crushes
After all, Perry told Diane Sawyer that he actually had crushes on all three of his female co-stars. "Well, how can you not have a crush on Jenny, and Courteney, and Lisa?” he said.
“So it made it kind of difficult to go to work because I had to pretend that I didn’t.” And he was particularly effusive about Kudrow.
Funniest person
The actor told Sawyer, “Lisa is the funniest, maybe the funniest person I’ve ever worked with, and just sees the world in a really funny way.” Perry said he received some nice text messages from his Friends co-stars about his book.
We wouldn’t expect anything less, considering how supportive the group usually is of one other.
A pack of penguins?
Perry told People in October 2022 that the group was even supportive during his darkest days. “They were understanding, and they were patient,” he said.
“It's like penguins. In nature, when one is sick or very injured, the other penguins surround it and prop it up and walk around until that penguin can walk on its own. And that’s kind of what the cast did for me.” And it's always been that way.
Best buddies
Speaking at the Summer TCA press tour in 2016, Matt LeBlanc told People that he still had a strong connection with his on-screen BFF, Perry. He said, “I love that guy!
I can not see him for five years and then get in a room together and still have that shorthand with each other. It's amazing, really. Ten years in a building with no windows and the doors locked, we got to know each other pretty well.”
Singing his praises
Kudrow was also keen to sing Perry’s praises in a 2019 chat with InStyle. She said, “On the last week of filming, Matthew actually gave me [Rachel and Monica’s] cookie jar as a wrap gift.
Everything on the set was technically owned by Warner Bros, so he had to ask special permission to take it. And that alone meant so much to me.” Yet it wasn’t all fun and games.
Getting snubbed
Perry and LeBlanc were notable for their absences at the 2015 wedding of Justin Theroux and Jennifer Aniston.
When asked at the Television Critics Association press tour about his no-show, Perry replied, “I wasn’t invited, so what can you do?” Perry failed to join the rest of his Friends co-stars a year later, too, at a tribute to one of the show’s directors, James Burrows.
His biggest nightmare
Perry also put a spanner in the works when it came to a potential Friends reunion. In 2016 he told Vanity Fair, “I have this recurring nightmare.
I’m not kidding about this. When I’m asleep, I have this nightmare that we do Friends again and nobody cares.” But he didn’t finish there; a refreshingly honest Perry continued talking about his nightmare.
Let sleeping dogs lie
He added, “We do a whole series, we come back, and nobody cares about it. So if anybody asks me, I’m gonna say no.
The thing is: we ended on such a high. We can’t beat it. Why would we go and do it again?” And to his credit, the cast never returned for a proper reboot of the original series. Even though they clearly do see one another a lot. The closest fans got to a reboot was the Friends reunion special filmed in 2021.
Meeting up with friends
In 2019 Courteney Cox practically broke the internet with a photo of herself and Perry. Referencing both Monica Geller and Chandler Bing’s famous catchphrases, the actress captioned the snap, “Guess who I had lunch with today...
I know!! Could I be any happier?” She concluded with the hashtag #realfriends. And several of their fellow Friends castmates were quick to respond to the photo.
Rumors resurface
Kudrow replied, “Lucky, lucky. #beautifulpeople,” while Aniston commented, “I love you, guys.”
Of course, the image also sparked a rumor that had previously surfaced several years beforehand. According to various sources, this was more proof that Perry was head-over-heels in love with his former on-screen wife. In fact, an unnamed insider apparently told Us Weekly that Perry’s feelings about Cox were nothing new.
An inside source
They allegedly said, “Matthew’s always been in love with her. Matthew has never fully been able to get over her.”
The source also apparently claimed that “any girl he’s tried to date looked similar to Courteney.” Reports about a possible romance between the pair actually first emerged in 2015 when Cox briefly split from singer/songwriter Johnny McDaid.
Lean on me
At the time, another anonymous source allegedly told blogger Perez Hilton, “It’s no surprise that Matthew was one of the first people Courteney called after Johnny left her. They’ve leaned on each other before.
There isn’t any pressure to put a label on it just yet, but they’re excited to see where this might go.” But was there any other evidence to back this up?
Body language
Body language expert Judi James believes there were signs of romantic feelings between the pair. She told The Sun in 2019, “A generation of fans identified with the Friends cast and grew up alongside them, meaning we part-believe their characters exist in real life.
It’s not hard to see that theirs has been a genuinely intense relationship.”
Taking a deeper look
James also pored over different photos of the pair to make her observations. She added, “At times their body language suggests sibling bonding with each looking out for the other.
Although there are some clues in their poses that the rumors of unrequited or even reciprocated love do hold water.”
Getting his act together
The National Enquirer also got in on the act with a story headlined, “Courteney’s Last-Ditch Plan To Save Matthew!” In the accompanying article, the long-running tabloid alleged that Cox had told Perry that “the door is open for a romance.” But there was apparently one condition.
According to the report, Perry apparently had to get his act together first.
Too much baggage
As yet another unnamed source supposedly explained, “She’s told Matt that he’s a charming, wonderful guy with a lot to offer. But she’s not interested in dating someone with too much baggage.
If Matt can stay sober for a sustained period of time and keep his nose clean, the word is Courteney will give him a shot.”
Wishful thinking
But such talk appeared to be somewhat wishful thinking. Given how much Perry revealed about his feelings in his memoir, it seems unlikely that he would have excluded a prolonged affair with his famous co-star.
Besides, the purpose of writing the book was, for Perry, much more altruistic. He did, after all, experience some of the darkest days imaginable, and he believed he could help others suffering in the same way. In fact, he wanted this — not Friends — to be his biggest legacy.
Hopes for the future
“It was important for me to do something that would help people,” Perry told Diane Sawyer. “I think [readers will] be surprised at how bad it got at certain times and how close to dying I came. I say in the book that if I did die, it would shock people, but it wouldn’t surprise anybody.
And that’s a very scary thing to be living with.”
Helping out
“So my hope is that people will relate to it, and know that this disease attacks everybody,” he continued. “It doesn’t matter if you’re successful or not successful, the disease doesn’t care.”
He even revealed how he tries to help others suffering in the real world. “I say, ‘Come over. Let's talk,’” Perry revealed. “And follow up, and help the person, and I see the light come on in their eyes. I have the answer because of stumbling so much. I could help them.”
His real legacy
“When I die, I don’t want Friends to be the first thing that’s mentioned,” Perry said in November 2022, just under a year before his untimely death. “The best thing about me, bar none, is that if somebody comes to me and says, ‘I can’t stop drinking, can you help me?’ I can say ‘yes’ and follow up and do it...
I want that to be the first thing that’s mentioned. And I’m gonna live the rest of my life proving that.” Perry added, “I would like to be remembered as somebody who lived well, loved well, was a seeker, and his paramount thing is that he wants to help people. That’s what I want.”