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Tim tries to explain why a prostitute named Debbie is in his apartment when his girlfriend, Amy, and her parents arrive home early from a cruise.
Trying to save face after his bachelor party fails to live up to expectations, a co-worker makes up a debauched tale that complicates Tim's life.
Tim agrees to pose as a Hispanic VP at the request of his boss, and Debbie helps him out with his charade.
Tim gets in hot water at Amy's sister's wedding by befriending an "unconventional" priest, and compounds matters during the reception by helping Amy's grandmother relive past memories.
Omnicorp'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 his bus seat to an elderly man backfires.
Tim get 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.
To properly size a Valentine's Day gift for Amy, Tim makes the mistake of giving her photo to Dr. Larry, a bra-store salesman.
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.
After a trip to Brooklyn, Amy accuses Tim of being anti-baby.
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.
