An unapologetic degenerate moves to affluent Greenwich, CT, to raise the outrageously spoiled kids of her wealthy sister and brother-in-law, who have fled the country to avoid prosecution for illegal activities.
When Mickey learns they've all forgotten Ben's seventh birthday, the family is forced to put their selfish tendencies aside for one day and throw him the celebration he deserves, which proves way harder than it sounds.
The Pembertons return to their country club to restore their family reputation, but Mickey gets into a fight with the phony country club ladies and Chip has been demoted from the champion golf foursome.
After Chip gets roped into a scandal, Sabrina leads a School Honor Board trial against him, where he must choose between snitching on his teammates or taking the fall. Meanwhile, Alba dents the family Bugatti, with Ben as a witness.
When it seems as though Chip is getting scammed by a girl he met online, Mickey tries to teach him how to be a "wolf" vs. a "sheep." Meanwhile, Sabrina is scared that her boyfriend is beginning to mirror Jimmy's ways and she plans an intervention.
The tables are turned when a cyber bully targets Sofia, leading Mickey to come up with a plan for revenge. Meanwhile, Jimmy teaches Chip and Ben how to be self-sufficient, resulting in a painful disaster.
Sabrina tells Mickey she wants to augment her figure, so Mickey decides the best way to dissuade her from doing so is to do a test-run in public. Meanwhile, Jimmy takes Chip and Ben to a baseball game to teach them how to be more masculine.