When his wife's book turns out a great laugh, but at the expense of his male pride, mayor Winston gets so depressed he is unfit to appear in public and must be replaced by his top aids. Superrich most eligible bachelor Tim Connelly is very pleased he thus spends an evening with Caitlin, who is attracted to him, except his embarrassingly boyish obsession with a SciFi series, which even means their next date is a fan convention. 

When Tim doesn't just propose another evening with Caitlin but a trip to St.Barts, she has her first real row with Charlie. After the press finds out the mayors limousine was carjacked with him, Paul and Charlie in it, PR demands they spend a night with an officer on patrol in a police car, while Stuart and Carter ride a police horse together.