What starts out as a normal, everyday office meeting turns into a huge enigma when the easygoing Jack suddenly loses his temper for no apparent reason and refuses to talk about it. The gang takes it upon themselves to discover the reason for his outburst, but with every lead they follow, the mystery just gets deeper and deeper. While this is going on, Finch tries to attract a pretty coworker by following Elliott's advice and playing hard to get.

Finch returns from Jamaica after a failed attempt at romance with Courtney, who played him, as it turns out. Elliott steps in to try to prove what a friend he is to Finch by giving her a dose of her own medicine--getting her hooked on him and then telling her to kiss off. Unfortunately, the plan goes awry when he ends up liking her and they start dating for real. Meanwhile, Jack makes another bet with Donald Trump--whoever loses less weight has to wear a dress during their golf game. However, he makes the mistake of asking Nina for help with his diet.