On the show, there wasn't any type of romantic connection between Chandler and Rachel, aside from a brief flashback moment. However, behind the camera, it was a different story as Perry crushed on his co-star. He knew the crush wasn't healthy and in addition, things only got worse when .
"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 something."
"Back then I got two jobs in one day – one was , an -type show, and the other was a sitcom. So I called Jennifer and I said, 'You're the first person I wanted to tell this to!' Looking back, it was clear that this made her think I liked her too much or in the wrong kind of way… and I only compounded the error by then asking her out."
Aniston wanted to be friends with Perry, while the actor admitted things became awkward after the moment took place and the crush was revealed. Nonetheless, Aniston was always looking out for Perry, especially during his darkest moments.
"What doesn't Matthew know?" Sawyer asks. "That he's alright," Aniston responds.
It was an emotional interview between the two. At the time, Matthew Perry's addiction battle had gone out to the public. Aniston broke down discussing the news, stating that the cast didn't know how to confront this type of problem given that it wasn't something they had faced in the past.
Aniston especially broke down thinking about the thought of potentially losing Perry to his addiction issues. It was an emotional interview and likely the hardest of Aniston's career. The moment can be seen below posted by
during his darkest times. She even approached him about his addiction issues on the set of .
Perry revealed with , “I had long since gotten over her – ever since she started dating Brad Pitt, I was fine – and had worked out exactly how long to look at her without it being awkward, but still, to be confronted by Jennifer Aniston was devastating. And I was confused."
“‘How can you tell?’ I said. I never worked drunk. ‘I’ve been trying to hide it."
Aniston would later reveal she smelled the alcohol on him. It was a tough moment for Perry realizing that the issue was affecting those around him as well.