For an episode of her Vogue web series Elettra's Goodness, the model met up with the Saturday Night Live comic, his girlfriend Alexi Ashe, and her brother Tolya Ashe.
The foursome split up into teams, opting for classic boys vs. girls showdown. The future host of NBC's Late Night predicted early on he would be the victor despite having never participated in a grilled cheese challenge before. "It's our first, but we've never lost one!" he said.
Of course, as the gals got to cooking, Seth had plenty of jokes. When Alexi, a human rights lawyer, commented: "It's smelling very good in here," he quickly quipped: "We can't smell past the mess you've made!"
But the gals had their fair share of fun too, throwing garlic at the guys to try and ruin their sizzling sandwich.
To be fair, the women had reason to sabotage. The men did have an obvious advantage being that Tolya is a personal chef.
Lucky for Seth, he opted to listen to the cooking guru instead of going with his own recipe which he listed as "Wonderbread, Crafts singles, Hellmann's Mayonnaise, set it on a radiator."
When all the fun and games were done the group broke (the cheese-soaked) bread while sharing pet photos and family traditions in this exclusive video.
Like how they tell each other there is food stuck in one's teeth. "It's an Ash family tradition to say ‘Teresa's calling,'" the 39-year-old comic reveals. Certainly seems classier than the point and tap method.
Another family tradition? Letting their dog Frisbee steal food from the table. "We're really impressed at how high she can jump for food!" Alexi says.
To see more of their hilarious meal and find out which team was declared victor in the grilled cheese challenge, check out the video above and watch the full episode on Vogue.com.