Matthew Perry portrayed one of the most charming characters on the comedy series Friends. As Chandler Bing, Perry excelled at impassive and self-deprecating jokes. This made him a delight and women found him attractive at the time, including Pretty Woman Star, Julia Roberts.

Before he starred in the iconic NBC sitcom, he was fairly unknown in the industry. Playing as Chandler has helped catapult his fame in the entertainment world. Matthew Perry's silliness as Chandler also captured the heart of Roberts. Their high-profile romance simply started with his humor and a bit of his knowledge on quantum physics.

Matthew Perry Was Awkward Around Women Back In The Day

Prior to starring in comedy series Friends, Matthew Perry had a hard time dating due to his awkwardness. The dating scene was painfully awful for the actor since he couldn't get someone to date him. He also believed that he's far from a conventionally attractive man. Aside from that, he's just awful with women since he's not comfortable with silence.

During the actor's interview Dateline in 2004, he said "I also am not comfortable with any silence at all.

I have to break any awkward moment or silence with a joke."

Thankfully, the show started picking up some steam that resulted to him rising to prominence. While the popularity of the show is on the rise, his cheerful and comical nature became attractive to women. He soon found himself in a series of high profile relationships in Hollywood that led to numerous gossips across the industry.

He said, "If you have dinner with someone and the next day the country thinks you're in a relationship, it gets a little weird. I was confused about dating before Friends. This all just makes it more confusing … [But], worst-case scenario, I still have the best job anyone could ever ask for.

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Matthew Perry Agreed To Julia Roberts' Strange Request, And She Appeared On Friends

Matthew Perry was the reason America's sweetheart Julia Roberts agreed to guest star on Friends. In 1996, Friends was among the most watched comedy shows on TV and the executives of the show capitalized on this fact and decided to air two-part special episodes as soon as the Super Bowl airing ended that year.

Since the NBC executives were keen on making the two-part episodes extra special, they knew they had to get a big celebrity to make the episode a more enticing one. And getting Julia Roberts to be on the show became their biggest goal that time.

The series co-creator Marta Kauffman said that they were so thankful that she agreed to do it and Matthew Perry had something to do with her decision.

On Kauffman's interview with The Hollywood Reporter, she said, "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."

The then NBC President Warren Littlefield also couldn't believe that the actress agreed to do it. He said, "I remember when I got a call and they said, 'Oh, we got Julia Roberts,' and it was like, 'Are you f—ng kidding me?'"

Show producer Kevin S.

Bright then detailed how Julia Roberts agreed to do it. The actress apparently accepted their offer under one condition.

Bright recalled, "Do you know the story of how we got her? Matthew (Perry) asked her to be on the show. She wrote back to him, 'Write me a paper on quantum physics, and I'll do it. My understanding is that Matthew went away and wrote a paper and faxed it to her the next day."

Julia Roberts Was Already Interested To Matthew Perry Prior Her 'Friends' Appearance

One of the most high profile relationship he's been in was his short-lived relationship with the A-list actress. As it turns out, the actress was already interested in Matthew Perry even before she guested on Friends.

Her interests towards the actor got deeper after the show. The staff writer of Friends Alex Junge revealed some behind the scene details.

He said, "They may have met before the episode, but she was interested in him from afar because he's so charming. There was a lot of flirting over faxing. 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."

Unfortunately, the couple broke up after a year of dating. They dated from 1995 to 1996 and Perry even detailed their romance on his memoir titled Friends, Lovers, and the Big Terrible Thing: A Memoir that was released late last year.