Mr. Sheffield and C.C. are going to Boston for the weekend, but what originally started as a romantic getaway plan for C.C. turned into family weekend thanks to Niles. Fran, Maggie and Niles have the house to themselves, and Fran decides to throw a singles party at the house to fish an eligible bachelor. But the party is over when an undercovered cop shows up and arrests Fran for not having the required licenses. After spending the night in jail, Fran returns home and Mr. Sheffield almost fires her, if it wasn't for Maggie stepping in and taking the responsibility for the mess. Fran goes to court, but Mr. Sheffield shows up in the last minute to help her from her senile lawyer, Uncle Mannie.

Fran's upset because Valentine's day is approaching, but she quickly turns to happy when she scores a date with Jeff, the cop. She encourages Mr. Sheffield to get a date himself, and shortly after an anonymous valentine's card appears on Fran's purse. She automatically thinks it's from Mr. Sheffield and gets a huge billboard sign asking for Mr. Sheffield to be her valentine. When she discovers the card was from Brighton's friend, Fran and Val rush to Times Square to try to erase the billboard before Mr. Sheffield sees it. Due to an accident, Fran is left hanging from a rope and Mr. Sheffield's the one that comes for the rescue.

Needing extra money for Yetta's bridal shower, Fran is hired by to be Chester's dog walker. As Fran and Gracie are strolling in Central Perk, a man distracts them and steals Chester. He asks for $20,000 for Chester to be returned safe, and for that much money Fran and Val decide to take over the investigation and rescue Chester themselves, but of course they also end up being kidnapped. Now the kidnapping couple is asking for $40,000 to return the ladies and the dog. Mr. Sheffield goes out for the rescue, but Fran gets rid of the kidnappers with some laxative chocolate Yetta gave her.