In this episode of The Hangout, Jonathan and Ayla cover everything from battling insomnia in the most unhinged way possible to plotting the perfect way to game the Disney parking system. Jonathan reflects on the sales drought at work, while Ayla reveals her new gig as a video podcast host for The Flyover—though her confidence takes a hit when she realizes her co-host casually owns eight Emmy Awards.

Meanwhile, Jonathan and his son have officially formed a band (Monster Teeth), but their hit song is currently lost in the void of his deleted voice memos. They also tackle a listener dilemma: Is it okay to return a bad Valentine's Day gift and use the refund to buy a dog just to spite your husband? Spoiler: Jonathan thinks this is not the way to introduce a pet to your home.

Then, it’s time for Richest Celebrity Kids, where Jonathan suffers through humiliating punishments (baby-voiced Luke Bryan and an Oscar-worthy reading of a lullaby) after wildly underestimating how much money Princess Charlotte is worth. The episode wraps up with a spelling test, a deep discussion on why Ayla hoards baby teeth, and Jonathan pondering why his own head is the size of a small moon.