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.