Day 5 (2016)

Episode Overview

Finch returns from Jamaica, disheartened after his romantic pursuit of Courtney backfires, revealing her deceit. Eager to support his friend, Elliott devises a scheme to turn the tables on Courtney by charming her and then rejecting her. However, the plan backfires when he unexpectedly develops feelings for her, leading to a genuine relationship. Concurrently, Jack engages in a weight-loss wager with Donald Trump, where the loser must don a dress during their golf match. In a misguided move, Jack enlists Nina's help for his diet, complicating the situation further.