Chandler and Monica were destined to be endgame, but there was a time when Matthew Perry had hoped Jennifer Aniston would be his endgame. Perry and Aniston are friends to this day, but Perry revealed that he once wanted to be more than friends, and even went so far as to ask Aniston on a date well before they had even stepped onto the set of Friends. In an Oct. 28 interview with Diane Sawyer, Perry opened up about his experience on Friends, substance abuse, relationships, and his new book, Friends, Lovers, and the Big Terrible Thing.
During the tell-all interview, Perry admitted that he had a crush on co-star Jennifer Aniston, who played fashionista extraordinaire, Rachel Green, on the hit sitcom. “Well, how can you not have a crush on Jenny?,” Perry began, before shouting out the other Friends leading ladies. “And Courteney (Cox)? And Lisa (Kudrow)? So it made it kind of difficult to go to work because I had to pretend that I didn’t have these crushes.”
Apparently, Perry’s crush on Aniston even led him to asked her out on a date. Before the two actors had been cast on Friends, Perry said he took his chance to ask Aniston out, but she squashed it, expressing that she would rather be friends — and that’s exactly what they became. Perry shared that Aniston was the first of his friends on set to confront him about his substance abuse and intervened when no one else did. “We know you're drinking,” he recalled her saying in his memoir, remembering her concern for his health during a dark period of time for him.
As it turns out, Perry wasn’t the only Friends star to have a crush on Jennifer Aniston. During the Friends reunion special on HBO Max in 2021, David Schwimmer admitted: “The first season, I had a major crush on Jen.” There’s a chance that in some way, Ross and Rachel could have been real, but the two actors decided not to pursue it. “At some point, we were both crushing hard on each other, but it was like two ships passing (in the night), because one of us was always in a relationship. We never crossed that boundary. We respected that.”
The most heartwarming part of these stories is that Jennifer Aniston always committed to her friendships with Perry and Schwimmer before even considering anything more. Perry and Aniston remain friends to this day, as was seen in the 2021 Friends reunion. Even though the possibility of a romantic connection is long gone, his recent interview with Diane Sawyer leaves room for fans to wonder if Perry’s crush on Aniston deserves a chapter in Friends, Lovers, and the Big Terrible Thing titled “the one where she gets away.”