Inside Matthew Perry And Jennifer Aniston's Real-Life Relationship

"Friends" star Matthew Perry passed away at age 54, and there's been an outpouring of both shock and sadness at his death. Perry's family released a heart-breaking statement, some of his friends and costars have posted tributes to Perry on social media, and the official "Friends" Instagram page shared a picture of Perry with the caption: "We are devastated to learn of Matthew Perry's passing. He was a true gift to us all. Our heart goes out to his family, loved ones, and all of his fans."

Perry was, of course, best known for his role as Chandler Bing on NBC's "Friends," but behind the funnyman character was a man who struggled with addiction for much of his life, including during his time on the hit sitcom. He told People about how much support and love he got from his castmates both during the show and after — the closeness of the six friends on-screen was mirrored by the friendships of the actors off-screen, and that included his real-life relationship with costar Jennifer Aniston.

If you or anyone you know needs help with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

Matthew Perry was once rejected by Jennifer Aniston

On "Friends," Jennifer Aniston's character Rachel Green dated two of the three other main male friends on the show — Ross Geller, played by David Schwimmer, and Joey Tribbiani, played by Matt LeBlanc. But Rachel never dated Chandler Bing, Matthew Perry's character. And while they never dated on the show, Perry did, for a time, want to date Aniston in real life.

He wrote in his memoir "Friends, Lovers, and the Big Terrible Thing" that he'd met Aniston three years before they were cast in "Friends." And he said that he'd liked her right away and ended up asking her out. But Aniston's feelings towards him were solidly in the friend zone, and she turned down his invitation.

In an interview with Diane Sawyer in 2022, he talked about how he had a crush on Aniston, as well as on Lisa Kudrow and Courtney Cox at various times. It was so bad when the show started, that he would even overthink how long he was allowed to look at Aniston on set before it got weird — "Is three seconds too long?" he quipped.

Jennifer Aniston confronted Matthew Perry about his drinking

Matthew Perry made it clear that he didn't drink or use drugs while he was working, but he did acknowledge that he would be on set hungover. And people noticed. Jennifer Aniston was the one who confronted Perry about his drinking after a few years into the show. She came to his trailer and told him, "We can smell it." Perry had thought that he'd been hiding it before that. True friends are ones that can and will tell you uncomfortable truths, so the bond between Aniston and Perry was strong.

Diane Sawyer spoke with Aniston in 2004, and Aniston acknowledged that while the show was going on, they didn't really know all that Perry was battling with addiction, though they knew some of it. And for what they did know, Aniston said, "We weren't equipped to deal with it." Aniston was asked what it was about each of her costars that they didn't realize about themselves, it was particularly touching to hear how Aniston spoke about Perry. Aniston said that what Perry didn't know about himself was, "that he's all right," and then she understandably got emotional. The amount of love that she had for him then, and surely still has now, seemed genuine and deep.

Matthew Perry was grateful for Jennifer Aniston's ongoing friendship

During the 2021 "Friends" reunion special on HBO Max, Matthew Perry talked about the closeness that he shared with all five of his costars, even after the show wrapped. "The best way that I can describe it is, after the show was over, at a party or any kind of social gathering, if one of us bumped into each other, that was it — that was the end of the night," Perry said. "You just sat with that person all night long" (via Newsweek).

But while he was clearly still good friends with all of them, he admitted to Diane Sawyer that after the show, Jennifer Aniston "was the one who reached out the most." Perry said that really meant a lot to him for Aniston to keep in touch and provide ongoing emotional support and love. We know there's no doubt that Aniston must be grieving for Perry after his tragic and unexpected passing.