The Life and Times of Tim features just that; the day-to-day life of an ordinary 25 year old New Yorker, trying to talk his way out of horribly embarrassing situations. Tim really has the worst luck, and his dry, dead-pan excuses are the centre piece of this show. Everybody makes mistakes, but for Tim just getting out of bed in the morning could be the worst decision he makes all day. No matter the situation, life's little challenges always manage to demand the most offensive solutions, which wouldn't be such a problem if he weren't continually caught red-handed.
Tim's inappropriate semi-formal attire and miscommunication over a shoot for GQ/GQ Magazine leads to more problems with OmniCorp; The priest returns with some gambling concerns that turn into problems for Tim
The boss uses a ruse to plan a heist to get Keith back from his ex-wife; Tim joins a fall foliage tour (with guest voice of Fred Willard) and embarrasses himself in several confusing mishaps.
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.
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 ends up with an assistant named Rodney; the boss goes to extremes to keep his dog following a divorce.