Carter sets the Mayor up with a woman who has a very personal history with the Winston Family. Caitlin and Charlie date a father and his daughter and end up in a family therapy session with them.
Charlie evaluates the staff to determine who is more worthy of a new office. Caitlin agrees to go on a date with a City Hall Santa who refuses to remove his costume.
Mike's good friend drops by for a visit after three years. But Mike's in the shock of a lifetime when he brings back more than just memories. Meanwhile, Paul teaches Stacy how to be cheap.
The country of Ghana is presenting the Central Park Zoo with a really smart monkey. When Mike insults Bobo's mother, the chimp is offended. Meanwhile Carter and Stuart spend Christmas together.
When Mike accidently swallows a Native American custom, he does everything he can to get the drugs out of his system when asked to take a urine sample.
Paul messes up a raffle drawing, so Mike has to make up for his mistake. Caitlin is blackmailed by Carter & Stuart. They plan to reveal her secret having been on Star Search. Meanwhile James sees Paul's dentist.