32: Amir vs. Jill in Jake Trivia (w/Jillian Vogel!)

·41 min·4 clips

Amir and Jill face off in a trivia battle to see who truly knows Jake Hurwitz better.

The episode begins with Jake and Amir introducing a trivia segment where Jillian Vogel, Jake's wife, faces off against Amir to determine who knows Jake better. They explain the rules: each gets eight questions, with points for correct answers and steals for wrong ones. The first question asks Jill for Jake's favorite movie, which she guesses incorrectly, leading to a steal by Amir. Questions cover Jake's apartments in New York City, his omelet order, OCD habits, favorite whiskey, and siblings' colleges. The score remains close, with both participants stealing points and making guesses. Midway, they take a break and resume with questions about shoe size, continents visited, and trips to Italy. The game intensifies as they approach the final questions, including one about Jake's triplet sisters' birth order and another about his favorite drink. The score ties at 7-7, leading to a tiebreaker where they must name Jake's two foot injuries. Jill provides detailed answers but faces a technicality debate. Since no clear winner emerges, they proceed to a second tiebreaker: naming Jake's high school friends. Jill wins by naming Frank after Amir runs out of names. After the game, Jill reveals she cheated by asking Jeff Rosenberg for friend names beforehand. The episode concludes with a secondary segment where Jake and Amir play a spelling game, interweaving letters of different words. They reflect on the trivia game's dynamics and Jill's victory, ending with promotional content for other HeadGum podcasts.

As heard by us

A Jake trivia game where the score keeps shifting and the whiskey question will not sit still.

Jake trivia becomes less a quiz than a personal scorekeeping match, with Amir and Jillian trying to prove who has the stronger claim on knowing Jake.

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Why you'd press play

Press play when one whiskey question sends a couples-and-friends trivia game into scorekeeping negotiations.

Read the full recommendation in PlayNext →

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