The love lives of Friends’ characters have kept audiences captivated for years now — but what was happening behind the scenes is just as intriguing. Although none of the stars of the beloved sitcom ever dated each other, they’ve opened up about some their underlying romantic feelings in the years since Friends ended in 2004. Notably, David Schwimmer and Jennifer Aniston revealed their real-life mutual crush in 2021, and more recently, Matthew Perry spoke with Diane Sawyer about how each of the three female Friends stars — Aniston, Courteney Cox, and Lisa Kudrow — captured his attention.
Before the group even started working together, Perry had already asked out, and been rejected by, Aniston. The actor wrote about the experience in his new memoir, Friends, Lovers, and the Big Terrible Thing, due out on Nov. 1, so Sawyer brought up how he “chain-crushed” on them during their sit-down that aired on Oct. 28. “Well, how can you not have a crush on Jenny? And Courteney? And Lisa?” Perry asked her.
The Seventeen Again star apparently attempted not to cross professional boundaries with his personal feelings, because he recalled trying to keep his crushes to himself. “It made it kind of difficult to go to work, because I had to pretend that I didn’t,” he added.
With Aniston, at least, the cat was long out of the bag. He wrote in his book that they met through acquaintances about three years prior to working on Friends together, per Entertainment Weekly. He was “immediately taken by her” and she seemed “intrigued, too.” However, after he called her to share his excitement about two jobs he’d booked and asked her out, he thought he’d “made her think [he] liked her too much.” Then, when she said she’d like to be friends, he told her, “We can’t be friends!”
The irony, of course, is that they did eventually become friends —and she was the one who reached out to him the most as he struggled with alcohol and prescription pill addiction during filming. Still, it was uncomfortable at times. “Fairly early in the making of Friends I realized that I was still crushing badly on Jennifer Aniston,” he wrote, per Page Six. “Our hellos and goodbyes became awkward.”
If this sounds like it could have been a plotline for Chandler, that’s no coincidence. Perry also told Sawyer about meeting with the show’s creators early on and admitting that relationships tended to be challenging for him. He told them, “Well, I’m not an ugly guy, but I have a lot of trouble with women.” To Sawyer, he added, “And that’s what Chandler became.”
Though his Sawyer interview and his memoir have some fun walks down Friends memory lane, Perry’s focus is sharing his experience with addiction. Speaking to GQ, he shared that he hopes to correct misconceptions about alcoholism and addiction. “It doesn’t decipher between the super wealthy or the guy who lives in the rent-controlled apartment,” he said. “It doesn’t care. It just goes randomly to whoever has the gene. And that’s a message I want out there.”