Tim tries to explain why a prostitute is in his apartment when his girlfriend Amy and her parents arrive home early; Trying to save face after his bachelor party falls short, a co-worker makes up a debauched tale that complicates Tim's life.
Tim agrees to pose as a Hispanic VP at his boss' request, and Debbie helps him out with his charade; Tim gets in hot water at the wedding of Amy's sister by befriending an unconventional priest and helping Amy's grandmother relive past memories.
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 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.
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 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.