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...
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 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.
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.
Looking 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.
Tim figures out a way for a Boy Scout troop to make Girl Scout-sized profits.
Rodney suspects his wife, Rochelle of cheating on him with a hockey player he admires.
An uninsured Tim gets medical attention from a womanizing doctor and a suicidal sales rep.
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.
Debbie 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.
Stu discovers he is an excellent table tennis player and uses his newfound skill to attract women.
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.
Tim becomes an assistant to a women's professional basketball player.
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.
Tim gets back 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.
Former Omnicorp employees file a class-action lawsuit with Tim as key witness.
Tim winds up with one Rodney as his assistant while Stu harasses the other.
After The Boss's divorce takes effect, he goes to extreme measures to keep his dog Keith.
In their new co-op building, Tim and Amy sign a VIP privacy form without knowing exactly whose confidentiality they are supposed to protect.
Amy and Tim host game night, which takes a strange turn when Tim disappears to buy Jenga despite inclement weather.
Amy and Tim go on a Vermont foliage tour with Stu and his new lady friend.
The debt-ridden priest for the NY Jets asks Tim to place wagers on his behalf.
After an ecological disaster involving Omnicorp, the company publicist chooses Tim to be the face of their apology.
HBO goes behind the scenes of their new animated comedy, The Life & Times of Tim and gives viewers a sneak preview of the upcoming pilot episode.
A man is confronted by his girlfriend, who has found a prostitute with him.
In an effort to win favor with Amy after she found him with Debbie the hooker, Tim visits her grandmother in the nursing home.
