Annie O'Donnell plays a single career woman living in New York City and searching for Mr. Right. In the season opener, Annie has a date with a homicide detective. It's a Saturday night, Annie meets him on the subway in car #3. She has said in the past that she'd never date a guy from the subway, or does she? Elliot got his wife Gail a gift certificate to the tire store for her birthday. Annie has named some pigeons, Bill and Hillary that she feeds on the window sill at her office. When Annie is getting ready for her date, Didi is giving her advice, like she always does, on what earrings to wear. Elliot and Gail help Didi paint her kitchen. Roger's date is so pleased with him that she gives him flowers.

When the gang comes to Annie's rescue after she finds a mouse in her apartment, they all end up playing a late night game of truth or dare. During the game, Annie accepts a challenge to ask a man out on a date, rather than identify the person about whom she had a sexual dream. When Annie fails miserably at the dating game, the rest of the group grapples with other dares: Elliot overcomes his shyness by walking through a bar in his brief, briefs. Roger overcomes his homophobia by getting a senual massage from another man, and Didi faces her fear of death by attending a stranger's funeral.

When Didi realizes that her irresponsible boy-friend isn't going to show up for her birthday, Annie O'Donnell uses a $100 off coupon and a virgin visa card with a $400 limit that she was saving for her honeymoon to treat Didi to a glamorous night at the Plaza Hotel. While the two girls attempt to live like queens on a serf budget, Roger and Elliot do some male bonding and discover that when it comes to women, they don't have anything in common.

Annie gets cold feet after she sees the webbed ones belonging to a doctor she's dating; and later finds that she wasn't the only one concerned about appearances. Meanwhile, Elliot has dreams about murdering Roger.

Annie has a bad cold, so what she really needs is rest, but what she gets is locked out of her apartment, as well as a request to check on a neighbor whose friends fear may be dead. Annie's flu forces her to try to spend a quiet day at home alone, but her apartment turns into Grand Central Terminal when each of her friends has a crisis and comes to her for advice. Annie's day is anything but restful when Elliot asks her to critique his latest short story, Roger finds a mole on his neck and thinks he is dying, and Didi has an emotional breakdown when Jim cancels a date.

Roger proposes to Annie after he learns that his 93 year old Italian grandmother, Nona Carlucci, is about to pass away and her last wish is to see him married. Annie reluctantly agrees to let Roger videotape a pretend wedding, but when roger sees Annie in a wedding dress, he realizes he is not ready for commitment and leaves Annie at the altar. Annie buys an antique armoire and Elliot buys an old ""C.H.I.P.s"" lunch box to relive his childhood, from the antique salesman.

When Didi's ex-husband shows up at her rent raising party, Annie, who didn't know he existed, feels betrayed by Didi and considers ending their friendship. Also at the party, Elliot, who is feeling rejected by his career-oriented wife, flirts with another woman, and Roger complains that he is being smothered by his lastest conquest, a woman he met only hours before.

When Roger narrowly escapes death after his mattress catches fire, Annie takes him shopping for a new one; but, when the two have a close encounter on a mattress in the department store. Roger interprets the incident as a sign from God. Convinced that God spared his life so he could start a relationship with Annie, Roger tells Annie that fate has brought them together. When Annie rejects him, he disappears and Annie, Didi and Elliot spend all night looking for him. Charlotte Rae, who played a house-mother to series star Nancy McKeon's character, ""Jo"" on ""The Facts of Life"" (1979-88), makes a cameo appearance as Helen, a bitter woman who applies for a job with Annie because her husband of 26 years recently left her for a blonde hygienist.

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When Annie confesses to Peter Calder that she doesn't want to see him anymore because he hunts doves, Peter promises to forgo the sport if Annie agrees to date him again. Annie's relationship is going great until Roger knocks Peter out during a sparing match and Peter tries to prove his masculinity by challenging Roger to another round. Meanwhile, Didi finds the ultimate job as a cosmetics salesperson and Elliot discovers that therapy is a great thing after he and wife go to a marriage counselor.

Annie plans a traditional Christmas at home with her dad, but but she find out the he had sold the old family house, in which she grew up in, she must finally face the facts of life and try to let go of the past. Annie fears that Christmas won't be as magical if she's not in her family home, so to make the holiday seem more traditional, Annie's dad buys her the biggest tree he can find without considering the true size of her apartment. Annie finds out that her dad has changed some of his old ways. He takes a train that's 3 hours earlier than his usual time. Insteed of his ""Bommer"" suite, that he has worned for years, he has bought a more fancy suit to wear to the China Grill, the most extravagant restaurant in town. Annie's brother went skiing for the holiday. Elliot and his wife Gail, on advice from their marriage counselor, stay away from his parents this Christmas.

It's shaping up to be a not-so-merry Christmas when Elliot's wife tells him she is going home alone for the holidays and Annie gets mad at Didi for quitting her job as a department store wrap girl. Elliot is bitter because Gail left him alone, and Annie and Didi aren't speaking, so Roger tries to get the gang in the holiday spirit by soliciting their help to play Santa and his elves during a Christmas dinner at his church's soup kitchen.

After the heating system stops working for 2 weeks in the building, Annie organizes a rent strike with the other tenants in the building. When that backfires and the water and electricity get turned off, she goes to The New York Hall of Records, room 702-A, to try and find the name of the owner of the building from the supervisor, Mrs N. Bradstock. Meanwhile, Elliot and Gail realize their marriage is over, so Roger invites Elliot to stay at his new apartment, but the odd couple living situation is more than Roger bargains for when he ends up being mother and maid to sloppy Elliot.

On her birthday, Annie is feeling that she isn't ""experiencing"" life, goes on a quest to fulfill some liflong dreams, but a central park carriage ride triggers her compassion for animals and land her in jail. Meanwhile, Roger assumes Annie will be doing her laundry as usual on Saturday night and plans a surprise party for her apartment, but when Annie doesn't come home, Roger fears the worst and calls the police

When the new boss disguises himself as a job applicant to spy on Annie, Roger and Elliot. The three fail the test miserably and worry that their jobs are in jeopardy when Mr. Barbour reveals his true identity. Mr. Barbour pushes the three to the edge as he institutes strict new office rules, but Annie puts her job on the line when Barbour tells her to stop placing clients like Didi, who quits just about every job after a day. Meanwhile, Roger threatens to quit when Barbour insists that all employees wear a polyester uniform.

When Didi lands a job assisting a famous playwright, Annie lands a date with a handsome actor and Elliot convinces Didi to show her new boss his play. Meanwhile, Roger considers mending his womanizing ways when he falls for an independent career woman who asks him out and then dumps him after only one date.

Annie is on cloud nine when her new boyfriend, Matt, promises her a Valentines Day night she won't forget; but, when Elliot's wife serves divorce papers that same day, Annie tries to split her time between Matt and Elliot, with disastrous results. Meanwhile, Roger and Didi decide to boycott Valentine's Day and spend the evening together, but when an obsesses ex-girlfriend stalks Roger all night, he and Didi seek refuge at a gay bar.

When Roger's father, Nick shows up unexpectedly, Annie tries to convince Roger that his dad probably wants to make up for lost time, but Roger can't help being suspicious of the father he has barely known. While Roger's dad is in town, Elliot moves in with Didi, but Didi immediately regrets inviting him after she excitedly appoints him her ""diet cop"" and he takes the job a little too seriously.

Annie thinks the black pearls she found in a taxi are fake but really belonged to Elizabeth Taylor.