Paul and Jamie Buchman are newlyweds living in a comfortable existence in a Manhattan high-rise apartment. Paul is a documentary film maker and Jamie is a public relations executive. After five months of marriage, Paul and Jamie are forced to schedule time alone together, only they both forget to cancel plans made with their friends in the building. Their friends are, Lisa Stemple, Jamie's older and equally neurotic single sister; Jay Selby, Paul's bachelor-slob friend, Dr. Mark Devanow, a wealthy gynecologist, and his wife Fran.
Jamie wants their first big purchase, a couch, to be a joint decision. At the store, Paul & Jamie and Fran and Mark wander through the store. Paul and Mark cover various subjects, and Jamie and Fran also talk of random things.
Paul has a dream that he and Jamie were just watching TV. Jamie interprets it to mean she is boring so Paul tries to find them something exciting to do. They make plans, but phone calls, visitors, and a parade hinder their outing.
Shelby tells Paul he saw Paul's old girlfriend, Lynn. Shelby is a restaurant with her and Paul & Jamie meet them. Paul is excited and nervous. Jamie is upset when he forgets to introduce her and he talks only to Lynn.
Jamie turns to a raving lunatic at the prospect of a visit from her meddlesome and obnoxious parents, so she invites her single older sister Lisa (who's even MORE neurotic and crazy then Jamie and Mr. and Mrs. Stemple combined), over to share in the experience with them.
Paul makes a documentary on Yankee Stadium for PBS. They do not like the film and reject it. Meanwhile, Jamie is working on a project and up for a promotion. She gets the promotion. Celebrate the promotion or feel bad about the rejection?
Someone Paul went to film school with is a token taker at the subway. Paul avoids the subway because he thinks the guy has a miserable life stuck in the subway rather than making films. Jamie gets tickets for the circus.
In this cross-over episode from the series "Seinfeld", Paul and Jamie become obsessed with dying and want each other to make a living will. Jamie soon learns that Paul is still subletting his old bachelor apartment and insists he settle the lease with the tenant... an odd man named Kramer.
Set entirely on a train during a getaway to Connecticut for Thanksgiving dinner with Paul and Jamie's parents, the long trip produces Jekyll/Hyde transformations for everyone when the passive Buchmans, Lisa and Selby and the bickering Devanows change in Act II during the trip back into the opposite mood.
Paul and Jamie get off on the wrong foot with their new neighbors: the uptight and snobbish Hal and Maggie Conway who move into the apartment across the hall from Paul and Jamie. The neurotic couple inadvertently make things worse with each new effort when they try to make the Conways their friends.
In a flashback to when Paul and Jamie first met at Christmas 1989, it's revealed that it wasn't love at first sight for them when Paul tries hard to persuade a reluctant, workaholic Jamie to leave her office and go out with him for the first time.
Jamie hires a maid to clean the apartment. Jamie loves her work, and Paul enjoys talking to her. He is taken with the fact that someone should have to clean up after their mess. Soon, Selby starts visiting and talking to her also.
New York City hires Jamie to create a tourist promotion commercial. She hires Paul so they can work together. Paul wants a code word for when they disagree, but she does not think they need one. They find it is too much togetherness.
Paul & Jamie take a weekend vacation. Jamie obsesses over leaving and what to pack while Paul tries to keep it simple. Once there, Jamie initially finds it hard to relax. Soon Jamie embraces the area and Paul wants to leave.
Paul & Jamie attend an afternoon wedding of a friend. Jamie thinks it is unorganized and starts changing things. Paul accidentally tells the father of the bride that the happy couple lived together before marriage.
On Valentine's Day, while getting ready for a party, Paul & Jamie get stuck in the bathroom when the doorknob breaks. They spend the time trying to break the door down, painting toenails, eating antacid pills for food and more.
Jerry Lewis guest stars as Freddie Statler, an extremely wealthy man. He wants Paul to film a documentary of his life. Paul hires a film editor/cameraman who turns out to be very low key and slow moving.
Paul is painfully embarrassed after an incident when his overbearing and eccentric father, Burt, causes a scene to get the attention of TV show hosts Regis and Joy Philbin and afterward, gets invited as a guest on their live TV talk show. As a result of the media attention, Burt is treated with support and compassion while Paul is treated with hostility by the press as the "disapproving son."
Paul finds out that Jamie has a former TV star as a client. Paul and Ira still adore the former spy girl from the show. At a dinner, Ira takes spy girl back to the apartment, but spy girl does not remember Ira the next day.
Paul feels no jealousy about leaving Jamie alone in the apartment with an ex-boyfriend of hers when she hires him to paint the place, but Paul gets an unpleasant surprise when he returns home from work and finds the guy in bed with, of all people... Fran. From then on, Paul and Jamie somehow get involved in finding out how Mark and Fran decided to split up.
Paul and Jamie's friends Fran and Mark are separating. Paul & Jamie listen to Fran one night, and Mark the next. Paul & Jamie plan their one year anniversary celebration. Jamie feels she is betraying their friends with her happiness.