Father Brian Finn (EDWARD NORTON) and Rabbi Jake Schram (BEN STILLER) have been best friends ever since growing up in Manhattan as kids. Despite coming from different religious backgrounds, the two get along fabulously well, and have instilled their sermons with enough enthusiasm that their services are packed. Even so, some members of Jake's temple, including Larry Friedman (RON RIFKIN), aren't crazy about his non-traditional methods, although the older and wise Rabbi Lewis (ELI WALLACH) tries to act somewhat as a peacemaker between the opposing views.
While Brian is obviously restricted by religious doctrine from having a girlfriend or wife, Jake is still an eligible bachelor, a fact that hasn't been overlooked by those in his congregation who want to fix him up with some eligible young Jewish woman, such as Bonnie Rose (HOLLAND TAYLOR) who wants him to date her daughter, Rachel (RENA SOFER), a network TV news reporter.
The one woman who had the most impact on either man's lives, however, was Anna Reilly (JENNA ELFMAN), a close childhood friend of theirs who moved away when they were still kids. Thus, when she returns to Manhattan's Upper West Side for a job assignment, their interest in her, as well as a hidden competition for her affection, returns.
While none of the three is immediately open with their feelings for the others, some complications do arise. For one, Jake's mother, Ruth (ANNE BANCROFT), hasn't spoken to his brother in several years since he married a non-Jewish woman, and finding himself in a similar situation doesn't sit well with him. Brian, on the other hand, finds his vow of celibacy coming into question, something he discusses with his superior, Father Havel (MILOS FORMAN).
As a secret relationship eventually develops between Anna and one of the men, the three must figure out how to deal with that romance and their friendship, while the two men must contemplate how all of that affects their religious future.