While Paul and Jamie are out at Riff's and around town testing pick-up techniques for Paul's new dating video, Ira squares off with Susannah, an old school friend of Jamie's, at the Buchman's apartment with each one refusing to let the other stay there alone.
In a flashback to January-March 1992, in the three months before Paul and Jamie's wedding, the chaos of planning the wedding only begins as the wedding invitations go out with a misspelling, then the menu choices are changed, no band is selected as well as no cake. Paul also pressures Jamie to quit her chain-smoking habit, who turns to binging.
With just one week left to Paul and Jamie's wedding, things get even worse when Jamie's wedding dress doesn't fit because of her binging habit. No band is still selected, and Paul's older sister, Debbie, leaves her husband. While Paul and Jamie try to keep both their meddlesome and obnoxious parents at bay, Ira and his friends treat Paul to a bachelor party at a local gentleman's club.
Lisa and Jamie seen to swap identities when they accidentally switch purses, leaving Jamie disorganized, Lisa suddenly competent, and Paul stuck without his passport just before he has to leave town to make a documentary on the Yukon wilderness.
Paul and Jamie are headed off to a tropical island resort given to them by Paul's parents, since they changed their minds about it and the trip is non-refundable, so Paul and Jamie have to pose as Burt and Sylvia Buchman. The trip has no TV or telephones and plenty of activities; Problem is the activities and the people who were matched to them are designed for Paul's parents. Jamie convinces Paul to play a game she used to do with Lisa when they were kids, where they would see how many different people they could be. Soon, they are saying that they are anything from ...
Ira's ex-wife, Marianne, returns where she is now a wealthy person after her second husband died and left her a fortune, which soon leads to a feud between Ira and Paul when Paul refuses to accept an interest-free loan from the recently widowed Marianne.
It's Paul's birthday once again and he lives in fear when this day comes every year; Not because he's a year older. but as he says, something bad always happens to him. Over the last four years, from 1991-94, we receive a "sample" of Paul's past birthday misfortunes and see why this "haunts" him every year since he was a kid; From Jamie almost leaving him, to having a catered party being given to him and only two people being there due to a freak spring snowstorm to having a surprise party thrown for him and is on the brink of crashing, due to a combination of ...
Paul is shooting a new movie about Pete, the last milkman in New York and neither he or Jamie can't seem to find time in their busy schedules, but they manage to plan on being together for pizza on Tuesday night. Meanwhile, Jamie and Fran have a new account, Ralphy's Diner and they're working on his new ad campaign. Ralphy tells Jamie and Fran that he's brought in a graphic artist as well, which turns out to be Jamie's ex-boyfriend Alan Tofsky. Both have different ideas for the as ad campaign and Lisa can see that this is not going to work out. When Jamie mentions ...
On their third wedding anniversary, Paul and Jamie go out with their friends to a strangely new ritzy nightclub called The Twilight Room. But afterward, Paul and Jamie's night out turns into "The Twilight Zone" when they slide in time into a parallel world where all evidence that they have ever met disappears, including their memories of each other. Now confined to this world as if Paul and Jamie never met; Paul is a free spirited man living with Ira, and Jamie is still a wealthy executive living with her boyfriend Alan.
Fran and Jamie have an interview with Lance Brockwell at City Hall. Paul is supposed to know him but cannot remember him. When he does, he visits Lance and it affects the job bid. Ira makes a bid on a store for expanding his business.
Paul & Jamie take Murray to a dog park to socialize with other dogs. Paul & Jamie meet the dog owners and find a new couple for double-dating. They offer show tickets to the couple when the tickets have already been offered to Fran and Ira.