How to Win a Double Date with Ben Affleck and Matt Damon (Now with Video)

For $10, you and a friend could win a dream date with Matt and Ben. Or Ben and Matt. Whatever.

Want to win a double date with Ben Affleck and Matt Damon? Well, here’s your chance. There are only five days left to enter a contest the pair’s promoting, most recently in the video above. (Mindy Kaling, I’m guessing, has entered 328,984 times already.)

Cambridge-natives-turned-Hollywood-heartthrobs Matt and Ben are following in the footsteps of another A-lister, George Clooney, by offering a dream date to one lucky contest winner. That’s right, you and friend could be flown out to Los Angeles for a “super secret, super cool Hollywood event” as Matt and Ben’s VIP guests.

In the new video, Matt and Ben (or Ben and Matt, because apparently order matters) bicker over who’s a more attractive date. Ben would like to “bore the shit out of you” with topics like 19th century literature and the Middle East (but he has more Oscars, and he’s Batman). Matt wants to talk about the Sox and Good Will Hunting.

The back-and-forth reaches a boiling point when Matt brings up Gigli. Jeez, way to hit below the belt. (Really though, don’t all our eyes twitch at the mention of Gigli?)

RELATED: The Oral History of Good Will Hunting.

Entries for the dream date cost $10 each (the same amount as Clooney’s dream date promotion), and benefit Matt and Ben’s pet organizations and the Eastern Congo Initiative. In other words, yes, of course this is for charity!

Even if you don’t win the dream date, you’ll sleep well knowing that you supported the two beloved Boston-area natives. Plus, if you ever run into the duo at the grocery store, you’ll have something to impress them with.

You: Matt and Ben!

Ben: It’s Ben and Matt.

You: Right, right. Oh my gosh, I love you guys so much. I even donated to both your charities!

Matt: Wicked awesome! Hey Ben, how do you like them apples?

Ben: Stop that.

You: Haha, but seriously, Good Will Hunting is my favorite movie.

Matt: Oh, you mean it’s not Gigli?

*Eye twitch.*


Contest ends February 18. Enter at, where you’ll also find all the fine print.