Maynard Gogarty is bored, with what he's not quite sure, but he's definitely bored. He's a tweed–suit–wearing, perennially glum thirty something living in a Manhattan flat secretly paid for by his crabby grandmother, and is nursing a short film career that shows no signs of development. Plus he's misanthropic and an unhappy dilettante – a real catch. But recently he's turned over a new leaf: he's decided, whatever befalls him, he's going to be happy.
Enter Jennica Green, who seems to have it all: a Princeton graduate with a high–paying city job and her own apartment. But then again, she's the kind of girl who spends two weeks organising a trip to a county fair, which might explain why she is single and looks like remaining so. When Maynard glimpses this Jewish Bridget Jones on a blazingly hot subway ride, what are the odds...?
Set either side of 9/11, Maynard and Jennica's courtship is narrated by our heroes and their many, many observers, among them all four parents (three living), a Russian–German–Israeli scam artist (and Maynard's current wife), a rapper with a linguistics background, a macaw, and an adolescent trumpeter. On the face of it, 'Maynard & Jennica' is about many things: a tree homicide, hip–hop sampling, the 1989 San Francisco earthquake, the Jewish intermarriage crisis, subway emergency brake etiquette, and the tournament rules of scrabble. At its heart though, it is a simple love story.