Tim tries to explain to his girlfriend and her parents, why a prostitute is in his apartment; Rodney tells Tim about his bachelor party, which Tim finds hard to believe.
Tim is asked by his boss to act like he's the Hispanic Vice President, of his company, and begrudgingly agrees; While at his girlfriends sister's wedding, Tim strikes up a conversation with an unconventional priest.
In order to get a promotion, Tim agrees to take his boss's daughter to her senior prom; Tim gets into fight with an elderly man, after trying to give him his seat on the bus.
Tim's co-workers give him a new nickname; While at a baptism, one of Tim's family members confesses something extremely embarrassing.
Stu invites Tim to join him on his first date with Marie, which Tim later regrets; While buying a Valentine's day gift for Amy, Tim makes a critical mistake.
Tim shows Bashko's daughter how to defend herself; Debbie tries to help Tim out when he messes up with his co-workers.
Rodney and Stu get Tim into trouble with an office prank; Tim shows Amy's dad a good time.
Tim's motivational speech at the office effects the mail guy's life in a bad way; Amy begins to think that Tim is anti-baby.
Tim ruins a mugger's life after he was attacked on the subway; Tim is sent on business trip with one of his older co-workers.
Tim's boss accuses him of having an affair with his wife, after the IT guy tells him so; Amy gives Tim a free pass, where he can sleep with any woman he wants, after Amy has a drunken affair.
While going through a rough patch after breaking up with Amy, at work Tim is threatened with being replaced by a hobo named Vince; Stu's pot dealer invites Tim and Stu to a play that he is in.
Searching for a place to crash, Tim ends up staying with the priest; Tim, Stu and Rodney visit Atlantic City to gamble and get girls.
Tim agrees to make a female firefighter look good by being carried out of an apartment fire; Tim is dragged into trouble after writing a note on a condolence card signed by his co-workers for Marie.
After being labeled "child hater" by co-workers, Tim is set to show them wrong; Rodney finds out that his wife is cheating on him.
Tim is caught in the middle of a battle between a sleazy doctor and a suicidal pharmaceutical sales rep; Amy goes overboard when she buys a gun.
The Boss goes to a jazz club with Tim, Stu and Rodney; Amy's colleague comes to regret his purchase of Tim's favorite bar.
Tim goes to the races and finds inspiration from Amy; Tim upsets an elephant trainer.
Debbie becomes a palm reader; Tim ruins the career of an escape artist.
Tim's Halloween costume is misinterpreted; Stu uses his newfound table tennis skills to attract women.
Tim loses his job when the chairman of omnicorp flies in from the UK; Tim befriends a well known Novelist.
Tim finds work as an assistant to a women's professional-basketball player; Tim decides he needs a haircut for a job interview.
Tim helps out with a ceremony for the Boss when he gets a city block named after him; Stu suspects his once-adoring nephew has changed his attitude since his Bar Mitzvah.
Tim competes with a teenager when he gets a job at the same golf course where he worked in high school; Tim invents a career as a sausage salesman to impress Amy's dad.
Tim helps an immigrant worker by posting flyers for jobs; Tim is a witness in a class-action lawsuit filed by former Omnicorp employees.
Rodney becomes Tim's assistant; The Boss is determined not to lose his dog, Keith, in a divorce settlement.
Tim is embarrassed by his past on a business trip; Tim and Amy move into a new co-op building, but are confused by a confidentiality agreement.
Tim's corporate credit-card bill breaks a company record; Game night at Amy and Tim's is interrupted when Tim ventures out in bad weather to buy a popular game.
The Boss's covert operation requires his employees' participation; Amy and Tim go on a fall-foliage tour in Vermont with Stu and his new girlfriend.
Tim is asked to pose for GQ magazine; The New York Jets' fiscally irresponsible priest wants Tim to place bets for him.
The Boss makes Tim's race an issue; A company publicist wants Tim to be Omnicorp's spokesperson after an environmental catastrophe.
