The Boss joins his 'bros'- Tim, Stu and Rodney - for a night out at an uptown jazz club; Amy's Jewish 'work husband' has buyer's remorse after buying Tim's favorite Irish bar.
Tim gets a new nickname after taking the rap for the misdeeds of his boss's dog; a momentary lapse at a family baptism turns into a major embarrassment for Tim, thanks again to the priest.
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 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.
The Boss gets a city block named after him, but needs Tim's help for the ceremony; Stu feels rejected by his Bar Mitzvah-aged nephew, who once idolized him.
The Boss invites Tim to be the 'token white boy'; after an ecological disaster involving Omnicorp, the company publicist chooses Tim to be the face of their apology.