11/13/2014 AT 11:30 AM EST
Turns out he didn't have to. You'll have to watch Damon's deadpan delivery in this video – and Affleck cracking up beside him – for the hilariously awkward answer. But suffice it to say Damon has always been quite impressed with his buddy.
"I always look at Ben and go, 'That's, that's something,' " he jokes.
The pair recently reunited to reveal the winner of season 4 of HBO's Project Greenlight, which will air next spring and follow Jason Mann as he directs a feature-length film, with Affleck and Damon as mentors.
With executive producers including Peter and Bobby Farrelly and Adaptive Studios co-founder Marc Joubert, the show is returning for the first time in a decade.
"Jason should be doing this, this is what he is meant to do, and he's really, really good at it," says Damon. "I think he's somebody who, in 25 years, we'll look back and he'll have made a lot of wonderful movies."
In fact, the series reminds the two stars of themselves when they were starting out, before their Oscar win for co-writing Good Will Hunting.
"We've known each other for more than 30 years, and the fact that we have a company together is kind of a part of the whole thing," Damon says. "We used to have business lunches together in high school when we had no business to talk about."
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