Onmicorp's boss agrees to give Tim a promotion--in exchange for taking his precocious daughter to her senior prom; Tim's well-intentioned decision to give an elderly man his bus seat backfires.

Tim regrets joining Stu on a first date with Marie, Omnicorp's strident HR lady; Tim makes the mistake of giving Amy's photo to Dr. Larry, a bra-store salesman, in order to properly size a Valentine's gift for her.

Tim shows his superintendent's daughter the ropes, on the job and off; when Tim messes up with his co-workers, Debbie tries to help him out.

Rodney and Stu get Tim into trouble with an office prank; Tim shows Amy's dad a good time.

Tim's pep talk ruins the mail guy's life; Amy accuses Tim of being anti-baby after a trip to Brooklyn.

Tim gets mugged on the subway, and ends up ruining the mugger's life; Tim goes on a business trip with an older colleague.

Tim offends the IT guy, who in turn implicates Tim in an affair with the boss' wife; Amy gives Tim a free pass after her own alcohol-induced indiscretion.