King George IV has a private moment where he divulges a deep insecurity of his. Roosevelt confesses a past insecurity he had about himself.

Debbie explains to Pete that she doesn't want to celebrate her 40th birthday early as she feels she is getting old.

Richard sees what happens to his plans and what his friend think of him when his jealousy gets in the way. Richard plan to get 123,000 downloads goes up in flames when Hooli's technical response team is called becuase Richard changed the background of Peacefare, an app made by Winnie's new boyfriend. Dinesh and Gilfoyle get angry because Richard declined Keenan Feldspar deal before he knew Keenan would pull the deal.

Richard sees Winnie at Hooli Con and is jealous of her new boyfriend who launches an app where you virtually help virtual people. Richard then sabotages his launch of his new app.

Doug and his friends learn to overcome their body insecurities.