June and Mark are obsessed with a reality dating show, and Chloe convinces June to go out there and actually get in the game herself. But when Chloe and June end up asking the same guy out, they get sucked into their very own pseudo dating show, with James orchestrating various dating challenges as they compete to win this guy's affection.

June is startled when a man she has never seen before jumps out of a door in the apartment that she has never seen before. It is Teddy, Chloe’s childhood friend from Camp C.U.T.S. (Callous Unemotional Trait Survivors) who visits her every year when he goes off his medications. His visit coincides with the Carter Marsh Annual Warehouse Sale, where Chloe uses psycho and manic Teddy to her advantage against all the vicious out of town women at the sale. Meanwhile, James is devastated when he finds out that his Beek Jeans have been relegated to the “cooling rack” at the sale where no one is buying them.