Jon Stewart, David Letterman Share Awkward Sex Scandal Moment [Video]

If you’re a fan of Jon Stewart, you know fairly well that he has a knack for making people uncomfortable on The Daily Show- although he’s usually doing it on purpose and with a totally salient point.

The usual targets for Jon Stewart are usually hedging politicians or pretentious pundits, and he’s gotten a lot of viral attention for incidents like the time when he went balls-out on Mad Money‘s Jim Cramer about the housing meltdown. (It was an epic burn that even an arctic lake of icy water could not soothe.) But Stewart is generally a pleasant interviewer and nice dude on his show, so it must of been hella embarrassing for him when he accidentally skewered David Letterman for being a horndog last night.

Stewart started out having a go at Mitt Romney, joking that Mittens looks like an underwear model. Then he segued into a bit about Letterman and underwear in general, riffing:

“Do you even have to wear underpants anymore? …I would think at this stage of your career, you just have people who can sit there and hug your groin for you. Just hold on. You got like a group of people — I’m sure, I got people who take a college credit for that.”

Now, knowing what we know about Letterman and his 2009 sex scandal involving relations with underlings, awkward. It’s likely Stewart just forgot and wasn’t being a dick, but ugh, painful to watch if true. Not least of all for Letterman, who squirmed and was visibly strained until finally actually just cutting Stewart off by reminding the fellow late-night host he had had a “little trouble along those lines” in the past.

Did the awkwardness stop there? No! Stewart then admitted:

“Can I tell you something terrible? I’m halfway through that bit and all of a sudden I realize, ‘what am I doing?'”

Clip below- check out how red Jon Stewart gets when the whole thing goes pear-shaped.