Caitlin and Charlie vie for an important account. Randall bonds with Paul during a father / son golf tournament. Carter helps Stuart write the script for a pornographic movie during working hours.

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.