Sly plans an emotional return to his childhood home of Philadelphia to show his children his humble roots. Scarlet embraces her newfound college independence and ditches the family trip... causing family turmoil.

As she gears up for her annual heart check-up, Sophia talks to Sly about the emotions surrounding her heart surgeries. Worried about his daughter's safety, Sly discourages Sistine from riding horses.

After several unsuccessful back surgeries, Sly goes under the knife again to repair a nagging injury. With Sophia's encouragement, Sistine goes on a live blind dating show hoping to find a man who isn't just dating her for her famous father.

Frank pays Sistine and Sophia a visit in New York, but quickly overstays his welcome. While Sly bonds with Scarlet's boyfriend in Palm Beach, Scarlet admits she's thinking about leaving Miami.

Inspired by the romantic atmosphere in Rome, Sly pulls out all the stops to woo Jen. Scarlet and Louis discuss the future of their relationship.

Sly worries that his fame will ruin the family vacation. In the aftermath of their fight, Scarlet worries that her relationship with Louis is in jeopardy.

With Sophia as her wing woman, Sistine goes on a series of dates to find love in New York City. Worried about moving to Florida and leaving Frank on his own, Jen sets out to find him a girlfriend.

Sophia struggles with a long-distance relationship and turns to her family for advice. The girls visit their Uncle Frank's unique house in an attempt to get to know him better.

The family is concerned about Scarlet spiraling after a break up and call on Sly to get involved; Sly accompanies Frank to his big concert in Atlantic City and worries that Frank's habitual bad luck will derail the show.

Sophia is worried that she will never live up to the success her parents have achieved and it starts to hurt her burgeoning literary career. Sistine finds success with her horror movie script, which causes a bit of sibling rivalry between her and Sophia.