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- Tim gets mugged on the subway, and ends up ruining the mugger's life; Tim goes on a business trip with an older colleague.
- 2008–201226mTV-MA8.2 (58)TV EpisodeThe 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.
- 2008–201225mTV-MA8.2 (63)TV EpisodeTim's Halloween costume is misinterpreted; Stu discovers he is an excellent table tennis player and uses his newfound skill to attract women.
- 2008–201221mTV-MA8.1 (74)TV EpisodeOnmicorp'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.
- 2008–201226mTV-MA8.1 (83)TV EpisodeTim 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.
- 2008–201224mTV-MA8.1 (64)TV EpisodeTim 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.
- 2008–201227mTV-MA8.1 (55)TV EpisodeThe 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.
- 2008–201226mTV-MA8.1 (56)TV EpisodeTim tries to help an immigrant worker posting job flyers; Former Omnicorp employees file a class-action lawsuit with Tim as key witness.
- 2008–201229mTV-MA8.1 (51)TV EpisodeThe Boss recruits his employees for a covert operation; Amy and Tim go on a Vermont foliage tour with Stu and his new lady friend.
- 2008–201229mTV-MA8.1 (46)TV EpisodeThe 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.
- 2008–201225mTV-MA8.0 (84)TV EpisodeTim 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.
- 2008–201227mTV-MA8.0 (61)TV EpisodeAn uninsured Tim gets medical attention from a womanizing doctor and a suicidal sales rep; Tim and Bashko pay for Amy's vigilantism.
- 2008–201226mTV-MA7.9 (67)TV EpisodeTim 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.
- 2008–201223mTV-MA7.9 (63)TV EpisodeRodney and Stu get Tim into trouble with an office prank; Tim shows Amy's dad a good time.
- 2008–201227mTV-MA7.9 (61)TV EpisodeTim gets back to his old high-school golf-course job and competes with a 14-year-old in a 'caddy-off;' To impress Amy's dad, Tim claims to have a lucrative career selling sausages.
- 2008–201228mTV-MA7.9 (45)TV EpisodeTim is invited to pose for 'GQ'; The debt-ridden priest for the NY Jets asks Tim to place wagers on his behalf.
- 2008–201225mTV-MA7.8 (67)TV EpisodeTim 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.
- 2008–201226mTV-MA7.8 (64)TV Episode(Season Two finale) Tim loses his job when the Chairman of Omnicorp flies in from the UK; Tim befriends a well known novelist, who inspires him to fulfill his dream of becoming a writer.
- 2008–201224mTV-MA7.7 (96)TV EpisodeTim's pep talk ruins the mail guy's life; Amy accuses Tim of being anti-baby after a trip to Brooklyn.
- 2008–201230mTV-MA7.7 (62)TV EpisodeLooking for a place to crash, Tim ends up with the Priest, who's about to give his first sermon since being suspended for having a girlfriend. Tim, Stu and Rodney run into a stripper version of Amy while playing hooky in Atlantic City.
- 2008–201228mTV-MA7.7 (61)TV EpisodeTim figures out a way for a boy-scout troupe to make girl-scout sized profits; Rodney suspects his wife Rochelle of cheating on him with a hockey player he admires.
- 2008–201226mTV-MA7.7 (56)TV Episode(Season Three Premiere) Tim becomes an assistant to a women's professional basketball player; Tim decides to go for a job interview haircut.
- 2008–201229mTV-MA7.7 (41)TV EpisodeTim winds up with one Rodney as his assistant while Stu harasses the other; After The Boss' divorce takes effect, he goes to extreme measures to keep his dog Keith.
- 2008–201225mTV-MA7.6 (112)TV EpisodeTim 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.
- 2008–201227mTV-MA7.6 (61)TV EpisodeA female firefighter takes undue credit for saving Tim's life; Tim becomes the scapegoat for a co-worker's deception.
- 2008–201225mTV-MA7.6 (46)TV EpisodeTim racks up a record-breaking corporate card bill; Amy and Tim host game night, which takes a strange turn when Tim disappears to buy Jenga despite inclement weather.
- 2008–201227mTV-MA7.5 (67)TV Episode(Season Two premiere) Tim finds that growing a post-breakup beard can have unexpected workplace consequences; Tim suffers through a bad play in order to help Stu score some pot.
- 2008–201226mTV-MA7.5 (116)TV EpisodeTim goes to the races and finds inspiration from Amy; Tim upsets an elephant trainer when the circus comes to Manhattan.
- 2008–201226mTV-MA7.5 (54)TV EpisodeDebbie becomes a palm reader and informs Tim of his fate in Staten Island; During a corporate retreat in Coney Island, Tim ruins the career of an escape artist.
- 2008–201229mTV-MA7.4 (98)TV EpisodeTim's past comes back to embarrass him while on a business trip; in their new co-op building, Tim and Amy sign a VIP privacy form without knowing exactly whose confidentiality they are supposed to protect.