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.

The Pemberton kids learn some lessons in "tough love," when Mickey calls in their overly strict grandmother to discipline them. Meanwhile, Mickey reunites with Jimmy.

Mickey tricks Sabrina into thinking she's pregnant to scare her into taking birth control. Meanwhile, Chip considers a vasectomy to thwart gold-diggers, but has not even kissed a girl.

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 Mickey believes Ben's school is discriminating against him, she stands up for her nephew. Meanwhile, Sabrina and Chip spend time with Alba and learn some surprising things about her.

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.