ENTERTAINMENT
02/03/2011 12:04 pm ET Updated May 25, 2011

Matthew Perry On 'The Daily Show': Masturbating Into Money, Setting Up Jennifer Aniston On A Date With Jon Stewart (VIDEO)

Maybe if Matthew Perry had a better idea how to spend his money, he might be a little bit happier...

Perry joined Jon Stewart on 'The Daily Show' on Wednesday to discuss his new show, 'Mr. Sunshine,' and, well, talk about how his life isn't so sunny. Or, at least his demeanor isn't.

Talking about a character based on his best friend, Mark Holder, whom he calls "an impossibly happy guy," Perry said that when Holder gives him his happy status updates, he tells him, "terrific, I'm going to go masturbate into some money."

Later on, Perry brought up a moment from his and Stewart's past -- Perry appeared years ago on Stewart's first talk show -- and remembered that Stewart once asked him to set him up on a date with Jennifer Aniston. Couldn't get it done, he said -- because he couldn't even get a date with Aniston himself.

Turns out, Stewart did it himself -- he and Aniston went on a group dinner date, which they laughed about back in August.

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