Jake sold his dreadlocks to pay his rent and everyone makes fun of his new hair cut. Bob is on vacation. Becker has taken up candy cigarettes. Linda explores religion when Chris's spell in the hospital makes her think about her own mortality. Jake runs into an old acquaintance, Hector, who always has a new scheme and won't just go and get himself a job. Chris tries to fight her ridiculous hospital bill, but ends up caving just like Becker predicted. Becker accidentally lets it slip that he told Chris that he loved her in the hospital, and then tries to explain it away as his being a comforting doctor. After a few days of torture, Becker realizes that Chris wasn't completely drugged up yet, and she meant it when she said I love you. They argue over the fact that she lied about it, and then he finally asks her out to dinner and she angrily accepts.

Chris finally pesters Becker into setting up their first date, and he promises her a romantic night at an Italian restaurant, but instead they spend the evening in a hospital when Becker has to attend to a patient. Chris feels like she's bonded with a Korean family that is concerned about their sick grandfather, but she doesn't realize that the family is celebrating when their grandfather finally dies. On Hector's advice, Jake becomes a guinea pig for drug-testing to make some money to pay the credit card bills that his ex-girlfriend left him with. Linda, who is considering becoming Jewish, makes Margaret feel guilty for flirting her way out of a speeding ticket.

Jake is horrified to find out that his grandmother died in her nursing home while having sex, but when he also finds out that his grandmother was sleeping with a number of different men in the home, his image of her is shattered forever. Chris tries to get Becker to be more romantic before they sleep together, but this just causes Becker to stress about the price of lobster at the restaurant she wants to go to. Becker finally makes a romantic gesture with wine, candelight and a bottle of wine on the fire escape, but he surprises Chris in the middle of the night when she's feeling less than romantically inclined.

After a number of failed attempts to have sex, Chris and Becker wonder if they're not meant to be in a romantic relationship. Jake is starting to annoy people with how much he's still mourning his nana. Linda uses feng shui to redecorate Becker's office.

Becker and Chris try to adjust to being in a relationship. They decide if they're going to make things work, they have to have some ground rules. Becker gives Chris a long list of superficial requests, and Chris asks Becker to try to be more considerate of her feelings. Margaret is worried that there is no spark in her relationship with her husband, Louis. When she accidentally finds herself working at a phone sex service, she is horrified when her husband calls. However, once Margaret learns about her own husband's fantasies, she is able to spice things up at home. When Jake accidentally gets a shipment of porn magazines to his newsstand, Hector starts selling them instead of sending them back as Jake asked.

Chris worries that Becker isn't opening up to her about anything, but Becker feels like their level of conversation is just fine, and finally has to tell Chris that he doesn't want to spend his evening rehashing the lousy things that happened at work that day. Linda meets a guy that she thinks is The One... until she meets his father, and then decides that his father is actually The One. Hector tries to get everyone to invest in coffee futures, but instead Jake lectures him on the value of a hard day's work and Hector watches coffee futures rise 300% without him.

Chris tricks Becker into having Thanksgiving at his place after promising to do all of the cooking and cleaning. Becker protests as Chris invites more and more people over, including her sister, Grace, that no one has ever heard of before. It turns out Grace just got out of prison for the attempted murder of her husband, and everyone worries when she quickly hooks up with Jake. During dinner, Chris and Grace get into a huge fight, and Chris accuses Grace of always being dependent on other people and never standing on her own two feet. Everyone else fears for their lives, but after storming off, Grace comes back and tells Chris that she was right.

When Becker's office and Chris's diner are filled with an unusual number of homeless people, Becker is enraged when he finds out that their neighborhood halfway house has been closed by the city. Becker tries to complain to the Deputy Secretary of Social Services, who politely (and then not so politely) tells him that there's nothing he can do. Jake's Nana leaves him $25,000 in her will, and after investing most of the money, Jake buys a $500 bottle of wine to share with his friends. Unfortunately, the wine tastes terrible.

Becker gets invited to speak at a medical conference in Las Vegas, and is thrilled when he gets a free first class plane ticket and a free suite at the MGM Grand. Chris is upset when Becker won't even considering trading in his first class ticket for two coach tickets and inviting her to come along. On his flight over, Becker meets a beautiful blonde doctor named Anna, but when she comes on to him in his hotel room he turns her down. Meanwhile, back in New York, Margaret deals with Becker's temporary replacement, a well-known plastic surgeon named Dr. Grath. Dr. Grath is amazed by Margaret's organizational skills, and offers her a high-paying position in his own office, but she turns him down because she finds his voice too annoying to work with every day. Becker comes back to town and Chris is still mad at him, and it doesn't help when Becker tells her about the hot doctor he didn't sleep with because of her. Finally, it takes an intervention by Jake to get them to see each other's point of view and apologize to each other.

Becker's office is flooded with patients wanting flu shots, but Margaret is out spending time with an old friend. Becker encourages Linda to learn how to give a shot, but when Linda has to give Chris a flu shot, they both chicken out and Becker ends up doing it. Margaret's old friend is now a successful designer, making Margaret depressed about not following her dream of being a singer. Becker comforts Margaret, reminding her that she is a valuable person and helps hundreds and hundreds of patients. Margaret gets some of her frustration out by singing at a local bar, and Becker is stunned by her beautiful voice. Hector gets a job as a doorman at a hot club, but gets fired after he angers the club owner's boyfriend. Jake and Chris fret over the unemployed Hector like they are his parents.

During a cold snap in New York, Chris convinces Becker to go on vacation with her to Bermuda. A reluctant Becker agrees to go, but is happy when a snow storm hits and it looks like they might be snowed-in. Chris finagles a way to get them out of New York and onto their connecting flight in Atlanta, and Becker admits that he tends to ruin relationships when he goes on vacation with a woman he's involved with. Chris tells him if they can't survive a vacation together, they don't really have a relationship, and drags him along with her. Becker ends up having a great time, but Chris's vacation is ruined when she sprains her ankle moments after arriving at the hotel. Linda's psychic tells her she'll meet the man of her dreams, but Linda just meets a cute bartender. Margaret is excited for a weekend alone when Louis goes to visit his brother, but she is surprised when she actually misses him.

Becker's old friend from medical school, Dickie, calls and says he's going to be in town with his wife Donna, and asks Becker if he'd like to have dinner. Becker accepts the invitation, and asks a flattered Chris to join him. Before the dinner, Becker goes downtown to NYU for a medical conference, and picks up Stevie Wonder tickets for Jake while he's there. On his way back to the Bronx on the subway, Becker is waylaid by a pathetic old lady who is trying to get downtown to Chambers Street but is confused and on an uptown train. Becker tries to give her directions, and then just takes her to Chambers Street himself. Once there, he stares at the woman as she looks at the stairs to the street and then just sits on a bench. She explains to Becker that she's come to look at the World Trade Center site since her son died there and today would have been his fortieth birthday. In the meantime, Jake is stuck back at the diner with no Stevie Wonder tickets for himself and his date, and Chris is stuck entertaining Dickie and his incredible bitch of a wife, Donna. Linda is working on the computer when an incredibly important file goes missing. Margaret, furious with Linda, works with tech support over the phone to recover the file, but once they look at the time stamp on the recovered file they realize it was Margaret that screwed it up, not Linda.

Becker becomes more introspective about his own life when he talks to one of his patients who has led a good life and is ready to die. Chris thinks that Becker is going to dump her when he asks her out to a nice dinner in the city, but both Chris and Becker are stunned when he tells her that he's actually realized that he's happy. Jake comes up with various frivolous ways to spend his inheritance from his grandmother, but, after getting some sense knocked into him by Margaret, he decides to go to college at Northwestern. Jake leaves his newsstand to Hector, who has turned down a job offer that he got using a fake resume. Linda meets a handsome Italian man and makes out with him constantly even though they can't communicate at all.