John and Chris reluctantly confront their feelings for each other in the sixth-season opener. Meanwhile, Chris is furious over an outrageously high hospital bill and tries to get some of the charges dismissed in a meeting with an unsympathetic hospital administrator (Paul Dooley). Jake sells his dreadlocks to pay his rent.

Chris pressures John into setting a time and a place for their first date, only to have it interrupted by a medical emergency; Hector talks Jake into making some extra money by participating in a drug test that goes terribly awry; Linda makes Margaret feel guilty about getting out of paying a traffic ticket.

John tries to plan a romantic first date with Chris, but unforeseen obstacles keep cropping up; Jake gets shocking news about his grandmother after she dies in a retirement home.

Jakes mourns for his nana; Becker and Chris try too hard to consummate their relationship; Linda feng shui's the office.

Chris gets frustrated when John repeatedly refuses to hold up his end of a conversation; Linda claims that she has met “the one,” but she soon gets a big surprise; and Hector tries to persuade Jake to invest in his latest get-rich-quick scheme.

Chris tries to get John to be more considerate of her feelings, but he's not sure he can do it; Hector tricks Jake into selling porn magazines; Margaret takes a night job with a telemarketer and is shocked when she learns that it's a phone-sex operation.

When odd characters begin to overrun Becker's office and Chris' diner, Margaret discovers that a local halfway-house has been shut down. Becker decides to round up his new eccentric friends and takes the law into his own hands with an organized march for justice. Meanwhile, Jake inherits $25,000 from his late grandma's estate and must decide what to do with the money.

Chris gets upset when John gets a free trip to Las Vegas to speak at a medical convention, but doesn't invite her to go along because he refuses to trade in his first-class airline ticket for two coach seats. Then Becker is tempted by a lovely doctor who whispers sweet nothings in his ear during the six-hour flight. Meanwhile, an uppity plastic surgeon takes over Becker's practice during his absence.

Margaret gets depressed and refuses to work after she learns that a long-time friend is now worth millions. The information leads her to ponder whether she could have made it as a professional singer if she had pursued her dream. Back at the office, John tries to train Linda to give flu shots.

There's a blizzard in New York, so Chris plans a trip to Bermuda with Becker; a psychic tells Linda she's going to meet the man of her dreams; Margaret looks forward to a weekend alone.

Becker meets an older woman on the subway who's on her way to Ground Zero; Chris entertains the doctor's out-of-town friends with whom he is supposed to have dinner; Linda accidentally deletes some important insurance files.

In the series finale, Becker realizes he's happy, but Chris fears that John is going to break up with her after he invites her to dinner at a nice restaurant; Jake used his inheritance from his grandmother to go off to Northwestern University; and Linda finds a new Italian boyfriend on the subway.