At the end of last season, John was thrown in jail for contempt of court during a malpractice case. Tonight, he's released after reluctantly apologizing to a judge, who orders him to see a therapist and work on his problem with authority. However, the therapist, Katherine Simmons, is dealing with her own authority issues, which John winds up 'helping' her work out. Becker is shocked one night when she shows up at his apartment a changed woman. Elsewhere, Jake grows weary of his new girlfriend's annoying habit of describing for him every little thing she's doing; and Linda lobbies for a raise.

John is more irritable than usual when he tries to quit smoking; Reggie believes a friendly customer stole all of her good luck and left her with his bad fortune.

Everyone's shocked when Jake announces that he got married over the weekend to a woman he met at a friend's wedding. After realising he may have rushed things, Jake gets an annulment.

A con man posing as a homeless person pulls on everyone's heart strings. Becker ignores his first instinct and comes to the aid of the man. Bob, Jake and Reggie chip in by offering money, a hot meal and advice; however, the man is not really homeless and the gang is shocked when his profession is revealed. Meanwhile, Margaret, in desperate need of extra cash, takes on a second job, then regrets it.

John takes Reggie's advice that he should tell women that he's sorry when he disappoints them, only to have it backfire; Jake and Bob switch jobs for the day.

John hurts his shoulder and is afraid to have an MRI, so Reggie goes with him for support; Linda dates identical twins.

Jake encounters a depressed man who is about to hang himself, so he takes him back to the diner to cheer him up; John learns that a patient's wife is pregnant by another man.

Reggie makes a special 'connection' with her friend's, Sara, husband. While Reggie and Becker are with another couple, Becker receives an emergency page and must rush off, reluctantly leaving his credit card to pay for the meal. Then Reggie's friend, Sara, also races off to tend to her children, leaving her husband Richard to stay and enjoy dinner with Reggie. But the two end up enjoying more than a meal-they end the night with a dessert that wasn't on the menu.

John believes he is finally in a perfect relationship after seeing Laura for several months. Their no-strings, no-pressure friendship is just right for him: it's filled with casual sex and devoid of responsibility. Unfortunately for John, it's no longer ideal for Laura. She wants a commitment, which is something John just isn't ready to make.
Elsewhere, Bob boasts about finding a Super Bowl ring in the backseat of a cab and plans to sell it rather than try to find its rightful owner; and Linda tries to talk her parents out of getting a divorce.

John reluctantly agrees to buy a poor child a Christmas gift and then discovers that he has to deliver it as well; Bob visits his mother, who still treats him like a kid.

John's day is filled with wacky people, from two guys who want a prescription for marijuana to a man who is upset when he learns that he isn't dying.

Reggie starts dating one of John's recently divorced friends, but can't stop obsessing about the guy's former wife.

John agrees to give free medical care to Bob, Reggie and Jake in exchange for repairs, food and magazines.

A tuxedo-clad John is on his way to his ex-wife's wedding in Connecticut when he stops in a bar because, in all honesty, he doesn't want to attend the event. Instead, the grumpy doc would prefer to have a few drinks, bend the ear of Frank the bartender for a while and get home in time to see the Knicks game on TV. And in the end, that's what he does, but not until he recalls (via flashbacks) his miserable Valentine's Day to Frank. While John complains about being all alone, the wise barkeep helps him realize how truly lucky he is.

John worries that women no longer find him attractive after Jake's girlfriend makes a disparaging remark to him; Linda fears that a pretty temp is going to replace her.

Parents are enraged when they learn that John's talk on nutrition to a class of 8-year-olds turns into a discussion about sex; two cops use the diner for a stakeout.

John is elated to learn that an article he submitted is being published in The New York Medical Journal, but when it appears, his article is accompanied by a picture of an overweight, unattractive stranger. After constant phone calls to correct the mistake, John is finally able to meet Wally, the editor, but then even more damage occurs. Meanwhile, Jake loses his hearing after going to a concert, and Linda is the dumpee-not the dumper-when she goes out Arnoldo the water delivery man.

When a patient loses the ability to speak, John gets him a machine that talks for him, but the man uses it to lash out at people; Bob turns into an environmentalist to impress a girl; Linda accuses Margaret of stealing her bracelet.

To Jake's horror, Reggie is obsessed with assisting him reach a goal he made up in the sixth grade. Reggie's persistence only causes pain and embarrassment for Jake, and she refuses to listen to John's pleas to leave Jake alone. Meanwhile, Linda drives the office crazy when she saves a patient's life and now thinks she can skip medical school and go straight to telling John and Margaret what to do.

Bob enlists the services of a questionable friend to get Reggie a great deal on a new freezer, under one condition. While trying to make a deal with Reggie, Bob's friend insults Reggie, teases Jake because he's blind and then threatens tohug the whole deal if Reggie doesn't go out with him on a date. Meanwhile, John finds himself acting as a sex therapist for the Bennetts, an 80-year-old couple having problems in the bedroom because of Mr. Bennett's newly revived libido.

Dr. John Becker's laundry, apartment and mail have all been tampered with and he is sure the culprit is one of his pesky neighbors. Determined to solve the mystery, he decides to confront all the tenants and barges into his building's weekly board meeting. Meanwhile Chris, the new girl in Becker's apartment building, is a hit with the gang at the diner, but her perky behavior only serves to darken his already miserable day.

When John receives eight expensive steaks from a patient, his new neighbor Chris compels him to throw a party.

John is surprisingly flustered when he learns that his upbeat neighbor Chris left town without saying goodbye. Reggie's woman's intuition kicks in and she immediately assumes that John has more than just casual feelings for his neighbor. Meanwhile, Linda sublets her job for a week to a girl who actually manages to do less work than Linda.

The fourth season concludes with a romantic cliffhanger as Reggie and a new neighbor (guest star Nancy Travis) each vie for John's affection. Also, Linda takes Margaret out for a night on the town, which Margaret lives to regret.