A Low Point In Matthew Perry's Dating Life Gave Friends One Of Its Funniest Moments

The entertainment world is still reeling from the sudden loss of Matthew Perry, the affable charmer who rose to fame as Chandler Bing on "Friends." The loss is greater considering that Perry was only 54 years old at the time of his passing, and how much closer fans felt towards him after his incredibly honest memoir, "Friends, Lovers, and the Big Terrible Thing," came out just last year. Perry's autobiography received most of its press due to Perry revealing, in great detail, his severe problems with alcohol and substance abuse. The book helped make the man behind the curtain, so to speak, just as likable as the onscreen persona that he'll be most remembered for. 

It's hard to imagine anyone else playing Chandler Bing at this point, and Perry wound up bringing a lot of his personal life to the part. As the show was ramping up for its first season, "Friends" creators Marta Kauffman and David Crane took each cast member out to lunch during the interim between the original pilot and the first episode to find out more about their real lives outside of the show. 

In the retrospective book "Friends 'til the End: The Official Celebration of All Ten Years" by David Wild, Perry remembered bringing up his love life, not knowing it would wind up leading to one of Chandler's most memorable moments. "They discovered who we were and what our lives were about," the actor recalled. "They said, 'Tell us something interesting about you, so maybe we can incorporate it into the show. I remember I wasn't doing very well dating at the time."

'I'm not an ugly man'

At that same lunch, the line between Chandler Bing and Matthew Perry began to blur when the creators noticed that Perry would always try and crack a joke anytime there was a semi-serious moment that came up. That same inclination became a major personality trait for Chandler once the show started to find its identity.

Directed by the legendary James Burrows ("Taxi," "Cheers," "Frasier"), the fourth episode of "Friends" features a line that Perry told to a friend after a bad date. When Perry gave Kaufman and Crane the details, it ended up in "The One with George Stephanopoulos" and became a signature moment for Chandler. In an interview featured in "Friends 'til the End," Perry remembered telling them, "I'm not an ugly man, but I don't do very well with women."

Perry also described his own dating life that wasn't exactly on fire during that time in his life before he became a network star.

"I had just been on a date the previous night. I got home, I called my friend and he said, 'How did the date go?' And I said, 'I'm going to die alone!' So then four episodes into 'Friends,' Chandler said that, and then we just kept going that way."

When Chandler says "I'm going to die alone!" early on in what became an epic ten-season run for "Friends," the audience hadn't quite fallen in love with the character yet. After that moment, there wasn't one person that couldn't relate to Chandler and the realities of single life, especially if they'd ever been on an awkward first date in New York City.