Caroline and Max try to secure winter lodging for Chestnut by finding him a job.
Carrie baby-sits for the boss' son; Doug tries to make friends with the new shoe girl (Rachel Dratch) at the bowling alley.
Doug dreams that he could solve all of his problems if he could assume the roles of vintage television characters.
Doug tries to prove to Carrie that he thinks about her all the time; friends threaten to ditch Doug's Super Bowl party for a co-worker's.
Doug starts acting like a child when Carrie goes on a business trip and his parents come for a visit.