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). Hector: Jorge Garcia.
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. Bong: Charles Chun. Nam: Kenneth Choi. Soon: Vivian Bang. Hector: Jorge Garcia.
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. Evans: Ed Bernard. Patrick: Fred Pinkard. Klein: Earl Schuman. Nelson: Jack Wallace.
John and Chris want to make love to each other, but unforeseen obstacles keep popping up to spoil the mood; Jake bores everyone with his constant grieving over his late grandmother. Ming: Ken Edward Rhoze. Tony: Juan Garcia. Rita: Jackie Debatin.
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. Doris: Kimmy Robertson. McCann: Wayne Thomas Yorke. Hector: Jorge Garcia.
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. Dana: Tamara Taylor. Joe: Joe Nieves. Gary: Aaron Fors.
Everyone gets nervous when Chris's younger sister (Jaime Pressly), who was recently released from prison for attempted murder, joins them for Thanksgiving dinner at John's apartment. O'Neal: Hal Lublin.
John's office and the diner are overrun with homeless people after a nearby residential-care facility is closed, so John goes to city hall to complain. Also: Jake receives a large check from his late grandma's estate and must decide what to do with the money. Customer: Chip Heller. Assistant: Christina Souza.
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. Back at the office, an uppity plastic surgeon (Gilbert Gottfried) takes over John's practice while he's away. Anna: Nicollette Sheridan. Victoria: Smith Cho.
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. Pianist: Harold Wheeler. Waitress: Helen Cates. Patient: Jeremy Lawrence. Margaret: Hattie Winston.
Chris wants to escape the cold weather, so she convinces John to go to Bermuda with her. But a snowstorm threatens to keep them stuck in New York, which is just fine with John. Chris: Nancy Travis. Hector: Jorge Garcia.
John tries to help an elderly woman on a subway find her way downtown, while Chris entertains the doctor's out-of-town friends with whom he is supposed to have dinner. At the office, Linda accidentally deletes some important insurance files. Naomi: Frances Sternhagen. Dickey: John Rubinstein. Donna: Molly Cheek.
In the series finale, Chris fears that John is going to break up with her after he invites her to dinner at a nice restaurant; Linda starts a torrid romance with a guy (Antonio Sabato Jr.) she meets on the subway who doesn't speak English; Jake surprises everyone with an announcement on how he is going to invest the money his grandmother left him. Gordon: Marvin Kaplan. Nurse: Susan Beaubian.