Win a Double-Date with Ben Affleck and Matt Damon – If You Can Stand Them

Win a Double-Date with Ben Affleck and Matt Damon – If You Can Stand Them
Ben Affleck (left) and Matt Damon

02/13/2014 AT 02:50 PM EST

Matt Damon and Ben Affleck: best friends – or frenemies?

The childhood pals jokingly infer the latter in this chuckle-inducing video that's a case study in one-upmanship.

The Oscar-winning duo are auctioning off a double date with themselves on Omaze.com to raise money for Affleck's Eastern Congo Initiative and Damon's water.org. The winner gets an all-expenses-paid trip to Los Angeles to see whether these two are really as insecure and bumbling as they seem here.

"It'll be like just us hanging out, taking selfies, talking about, how, like, the Sox are going to do," Damon explains on camera about what the winner can expect to happen.



Affleck promptly scorns Damon's seemingly bourgeois suggestions and counters that they could instead talk about "19th century literature, or the current state of politics in the Middle East." Later, Affleck also suggests that the duo could ask the winner "meaningful questions like, 'What are your hopes? What are your dreams? What are your fears?' "

Damon appears to roll his eyes at his pompous friend, and doubles down on his everyman approach. "If you don't want to get really weirded out by having existential questions posed to you by Ben Affleck, then maybe we could talk about some other fun stuff, like stories from the set of The Bourne Identity,' or any of the other hit movies I've been in.' "

Not to worry: Affleck didn't take that dig lying down. He then declared they could talk about stories from the set of Argo, which he pointedly notes won Best Picture – as Damon shoots him a withering look.



Things devolve from there, as Affleck pokes fun at Damon's height, Damon mocks Gigli and so on.

The folks at Omaze are clearly in on the joke, as they advertise the experience as a chance to learn, "What it’s like to act, write, grow up in Boston, play poker, vacation, get named Sexiest Man Alive, win Oscars and be epic … all with your best friend."

Entry cost? $10. The experience to hang out with this cunning duo? Priceless.

MORE ON: Ben Affleck , Matt Damon

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