In this episode, Matt is joined by his childhood best friend, Ben Shore, who’s been around since sixth grade and knows all the stories Matt would probably rather forget. From middle school to college and every chaotic phase in between, their friendship has survived it all.

Together, they reflect on what it takes to maintain and create new adult friendships, share a few ridiculous (and questionably appropriate) stories, and introduce a new game segment: Would You Rather. Along the way, Matt opens up in a way he hasn’t before—making this episode equal parts hilarious and unexpectedly heartfelt.