New Year's Day (1989)
A man returns to his sublet apartment to find the previous tenants, three offbeat young women, still in residence, under the mistaken belief that they have the apartment until the end of New Year's Day.
Drew is a recently divorced middle-aged Hollywood writer/director who arrives back in New York looking for a path to start his life over and upon arriving at his old apartment, finds three young women residing there until the end of the day. They are the free-spirited Lucy a multi-career woman and part-time actress who wants to move to Hollywood to start her life over; Annie is a photographer Lucy's best friend who wants to move to L.A. with Lucy, but unsure at what she wants to do with her life; Winona is a 30-year-old magazine editor who feels her biological clock ticking and wants to start a family. On his long day, an assortment of people soon arrive at the apartment for a party where they talk amongst each other about their stance in life in which Drew sees the inspiration from the conversations on deciding to start his life over.
- Drew (Henry Jaglom), a writer living in California, is miserable and decides to move back to his home town, New York City. Exhausted from an all-night flight, Drew arrives on New Year's Day, only to be greeted at the door by Winona (Melanie Winter), one of three previous tenants still living in the apartment. Winona explains they have the place through the first, but Drew insists that means they were to vacate by the first. Winona brews them tea, and the other two roommates, Annie (Gwen Welles) and Lucy (Maggie Jakobson) come out in their sleepwear. They tell Drew they cannot leave because they are throwing a going away party for Lucy, who is moving to Los Angeles, California. Drew agrees to give them the extra day and telephones various hotels to rent a room.
Annie informs Lucy she is giving up alcohol and sugar as her New Year's resolution, and Lucy responds that she is giving up men. After explaining to Drew that her "biological" depression always starts the week before Thanksgiving and ends New Year's Eve, Annie suggests they share the apartment for one day. Since Drew cannot find a hotel vacancy, he agrees.
During their conversation, Drew discovers Annie is a public relations representative for an art gallery, Lucy is a voice-over artist for Saturday morning cartoons, and Winona is a photographer, who is planning to get pregnant by a "genetically perfect" man in the New Year. Lucy offers Drew her room to sleep in while she packs. Before falling asleep, Drew sees Lucy watching a videotape of herself swimming with dolphins. She explains the dolphins got aroused and tried to have sex with her.
As Drew sleeps, Lucy's parents and others arrive for the party. Among them are Dr. Stadthagen (Michael Emil), a therapist who believes he has to have sex with a woman to see if they are compatible for therapy; a delivery man who does not leave (Robert Hallak); and Lucy's former boyfriend, Billy (David Duchovny). Lucy takes Billy aside to ask why he showed up and he tells her he loves her. She cannot forgive him for his infidelities and he counters that she also cheated on him. Drew overhears the argument which ends with Lucy and Billy kissing.
After Billy goes to the bathroom, Lucy tells Drew she is going to California to get away from a no win situation. Drew confesses he came to New York City to start over again after his divorce, but believes he is too old to start over at age 45. Lucy disagrees. They are interrupted when Lucy's father, Bruce (Harvey Miller), demands to speak with her. As he begs her to stay in New York, more people arrive and Lucy leaves to greet them. Bruce asks Winona's help in getting his daughter to stay, but she insists Lucy has to experience life to become an adult.
When their landlord, Lazlo (Milos Forman), arrives with champagne, the girls swarm him to say how much they will miss him. Annie reminds Lazlo how one night she crawled into his bed, but the older man could not get an erection, so they just held each other. More people arrive and Lucy spies Billy flirting with her friend Marjorie (Tracy Reiner). Later she sees them kissing in the hallway. She answers the door and finds her psychologist. They go into the kitchen and she tells him how she worries that leaving Billy is a mistake because they share a true love. She fears that if she leaves Billy, he will find another girl because he cannot be alone. She also confesses feeling guilty about leaving her parents and Annie. The doctor tells her that although these people are important, they are not more important than being true to herself.
Meanwhile, Drew takes Billy aside and gets him to confess that he is pretending to be "dark" because he is afraid others find him boring. In another room, Winona confesses to her big brother, Harlan, that she is planning on becoming a single mother. He reminds her of the pain they felt when their mother left, but Winona insists they did okay.
Later, Lucy confronts Marjorie about Billy and tells her to leave. She walks into the living room to see her father and Billy both trying to seduce women. As various couples pair off, Lucy drinks alone. When Annie asks Lazlo to sing her a Hungarian lullaby, Lucy goes into her room to find Drew in her bed. He tells Lucy he is attracted to her and she kisses him. After a few minutes, she breaks away, telling him she cannot make love to him. Drew tells her it is alright and holds her until they fall asleep.
Meanwhile, Annie brings Billy into her room and tells him she finds him sexy and confesses she also had these feelings about her father. Billy asks her to join him in the bed and they embrace. Later, everyone else is gone when Lucy wakes up and walks into Annie's room to find her making love to Billy. She explodes and throws a naked Billy into the hall. She goes to fight with Annie, but finds her in the bathtub with an empty pill bottle. Drew joins them and Lucy orders him to get some coffee. Lucy tries to get her roommate to reveal how many pills she swallowed. Instead, Annie kisses Lucy and tells her she had sex with Billy because she really wanted to make love to Lucy... thus revealing that Annie is a lesbian and has had a crush on Lucy this whole time. She asks Lucy to kiss her back. Lucy does. Lucy tells Drew there were only a few pills left in the bottle and Annie will be alright.
In the final scene, Drew asks what Lucy plans to do. She insists she is still going to Los Angeles to find a place to live. Drew gives her the keys to his California house and asks her to telephone him now and then. After she leaves the room, Drew watches the videotape of Lucy swimming with the dolphins.