Sly and Jen decide to pack up and move to Florida full time, but the prospect of leaving his home for good fills Sly with doubt; Sly worries about Sistine and Sophia's safety and puts them through a rigorous boot camp.

Scarlet's new boyfriend comes to town, and struggles to win Sly's acceptance. Sophia confronts her mom over feeling pressured to settle down and have kids.

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.

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.

Scarlet and Sistine are determined to help Sophia get over her debilitating fear of public speaking. Sly fears his celebrity is preventing him from being taken seriously as a fine artist.

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.

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 concludes his romantic gestures by throwing Jen a love ceremony. Sophia goes on a date with an Italian man. The family pays a visit to the Pope.