Keeping the Faith is a 2000 romantic comedy.
- Ben Stiller - Rabbi Jake Schram
- Jenna Elfman - Anna Riley
- Anne Bancroft - Ruth Schram
- Miloš Forman - Father Havel
- Eli Wallach - Rabbi Ben Lewis
- Brian George - Paulie Chopra
The film begins with a drunken and downtrodden Catholic priest telling his story to a sympathetic bartender. Father Brian Finn has been dedicated to his calling since he was a child and now shares the duties of a New York parish with an older priest, Fr. Havel. Rabbi Jacob "Jake" Schram, best friends with Brian since childhood, is the youngest rabbi at his Conservative synagogue; his lack of effort to find a Jewish wife often results in his mother, Ruth and other women of his congregation setting him up on blind dates, much to his dismay. The two men show a close bond, even in their professions, where the two are planning the opening of a jointly sponsored community center. In its earlier days, the friendship included a third party. Via flashbacks and reminiscent musings, Anna Reilly is introduced: she met Jake and Brian in middle school, after beating up a bully who was picking on them. The three became great friends, and enjoyed their childhood together. Unfortunately, Anna's father got a new job that resulted in the Reillys moving to California, and ultimately she lost touch with Brian and Jake.
Sixteen years later, Anna calls her old friends out of the blue and the friendship is rekindled when her company temporarily reassigns her to a New York position. Feelings quickly begin to run deeper than before, as Anna, despite her workaholic tendencies, is as vibrant as Brian and Jake remembered her; however, it is, ironically, the men's careers that prove to be the most problematic. She and Jake begin sleeping together, but he is reluctant to be involved in a serious relationship with her because she is not Jewish, a fact which could compromise his relationship with his congregation and also with his mother (who disowned her eldest son - Jake's older brother Ethan - for marrying outside the faith). Between the religious conflict and their desire to spare the feelings of their mutual friend, the relationship is kept mostly secret, resulting in both humorous and harmful complications. As the months pass, both Jake and Anna's feelings for each other become stronger but due to the aforementioned issues, Jake still refuses the relationship as a serious one, despite Anna dropping hints to him about her having been recently taking a class (but refusing to tell him what kind of class it is), and her becoming visibly upset when they run into members of Jake's congregation while on a date and Jake introducing her only as "my old friend Anna".
Meanwhile, Brian is involved in his own test of faith as he struggles with his feelings for Anna despite his vows. Apart from praying about the situation and discussing it with Fr. Havel, he keeps these thoughts mostly to himself. Brian begins misinterpreting Anna's words and actions (some of which are subtle signals to Jake as their affair is kept under wraps) and even has an erotic dream about her; he begins to seriously consider quitting the priesthood to pursue a romantic relationship with her. Anna tells Jake that she wants things to be more serious between them and he does not respond well. While the three have dinner one night with Jake's mother Ruth, Ruth has a private conversation with Anna, where she tearfully reveals that she knows about Anna and Jake's secret relationship. Jake and Brian walk in on the ladies having a tearful moment, and later Jake and Anna have an argument over the religious issues complicating their romance, which ends in the two parting ways in frustration. Anna calls Brian for comfort and he rushes over to her apartment. Still unaware of what's been going on, he takes her tearful ramblings to be a confession of feelings for him, then kisses her and admits his love. When she interrupts him, he first assumes it to be guilt based on his vows, but she tells him she is in love with Jake and finally admits that she and Jake have been seeing each other secretly for months. Feeling embarrassed and rejected, Brian raids Anna's liquor cabinet, angrily cutting off her attempts to re-assure him and apologize. He leaves and spends the whole night out drinking on the streets. The next day, still drunk, Brian stumbles into Jake's temple and interrupts a post-bar mitzvah gathering, resulting in a confrontation with Jake that ends with the priest punching the rabbi. He leaves and stumbles around the city, which brings the movie back to the very first scene with the bartender.
As the Community Center's grand opening approaches, along with the last days of Anna's East Coast assignment, the relationships begin to mend, first with Jake reconciling with Brian, followed by Anna reconciling with Brian shortly after. A discussion between the two men prompts Jake to go to Anna's office building, with Brian shouting encouragement at him as he runs down the street. Jake interrupts Anna's going away office party and manages to get her attention from a window in the building across the street and calls to explain himself and offer to set things right. Later that evening, they surprise Brian in the middle of his karaoke number at the interfaith center, which looks to be off to a successful start. Anna greets Rabbi Lewis as he passes by and asks about their meetings together, referencing the class that Anna had told Jake briefly she had been taking, at which point it becomes clear that she had been taking classes to convert to Judaism. She tells him she hopes to pick it up again as she is also now staying in New York, with Jake clearly thrilled. The film ends happily with the three childhood friends posing for a photo together.
- "Ready to Take a Chance Again" - Father Brian and Dang