Matthew Perry played one of the funniest characters on Friends. He excelled at deadpan, self-deprecating humor that truly made Chandler Bing a delight. And as it turns out, that sense of silliness extended to his life beyond the set.

Perry was relatively unknown in Hollywood before getting cast in the iconic NBC sitcom. Playing Chandler helped catapult the actor to fame, and the role even led to a few high profile romances with fellow Hollywood stars.

The Friends alum even hooked up with A-lister Julia Roberts, and it was all thanks to funny jokes and a bit of quantum physics.

Before his role of Chandler made Perry a superstar, the actor struggled with feelings of awkwardness in his dating life.

During the early stages of Friends he told show creators that while he was not an unattractive man, he did feel just awful with women, InTouch reported.

I also am not comfortable with any silence at all, Perry said during a 2004 Dateline interview. I have to break any awkward moment or silence with a joke.

Eventually, Perrys jovial nature attracted multiple romantic partners. Goofing around even led to a long term relationship with Roberts.

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By 1996, Friends was one of the hottest comedies on television. NBC execs decided to capitalize on that popularity by airing a special 2-part episode immediately following the Super Bowl game that year. And they knew they needed some special celebrity guest stars to make it even more enticing.

Getting Julia Roberts was incredibly exciting. We knew she would have the right touch for it. And when she said yes, it was pretty awesome, series co-creator Marta Kauffman told The Hollywood Reporter.

Producer Kevin S. Bright followed up with a funny story about how that happened. Do you know the story of how we got her? Matthew (Perry) asked her to be on the show, Bright recalled.

She wrote back to him, Write me a paper on quantum physics and Ill do it. My understanding is that Matthew went away and wrote a paper and faxed it to her the next day.

Roberts played Perrys love interest in the Friends episode titled The One After the Super Bowl. And their playful banter didnt end there. After filming wrapped, the two actors stayed in touch and eventually began a romantic relationship.

There was a lot of flirting over faxing, writer Alexa Junge told THR. She was giving him these questionnaires like, Why should I go out with you? And everyone in the writers room helped him explain to her why. He could do pretty well without us, but there was no question we were on Team Matthew and trying to make it happen for him.

Perry and Roberts dated for about one year, doing their best to keep the relationship hidden from nosy tabloid reporters. And it was all thanks to Perrys sense of humor channeled through Chandler.

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'Friends' Star Matthew Perry Dated Julia Roberts By Wooing Her With Quantum Physics and Funny Jokes - Showbiz Cheat Sheet