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Jake: Let me just say....oy.
Brian: Amen to your oy.
Brian Finn and Jacob Schram are at the mercy of a schoolyard bully when Anna Riley arrives to stop him. The three become inseperable friends, until Anna's father takes a job in California and she moves away. Brian and Jacob stay best friends, grow up and enter into their respective careers: Brian becomes a Catholic priest and Jacob a rabbi. When Anna returns to New York for work and re-connects with her friends, Triang Relations ensue.
A spin of sorts on the 'A priest and a rabbi' jokes.
- The Bartender: Pauly, who accordingly listens to Brian's story and dispenses advice when he's finished.
- Chekhov's Gun: The skyscraper across from Anna's office with the windows that can be looked into becomes important in the climax of the film.
- Confessional: Brian is seen hearing confessions at his parish, though when he sees Anna in the booth after he kissed her and she confessed she was in love with Jake, he balks.
Brian: Excuse me if I say that I don't think I'm the best person to offer objective advice on this particular confession.
- Converting for Love: Strongly implied with Anna.
- Cool Teacher: Jake, when he's helping a young member of his congregation learn a Haftarah for his Bar Mitzvah.
- Did Not Get the Girl: Brian
- Erotic Dream: Brian has one about Anna.
- Forceful Kiss: Brian does this to Anna, thinking she's about to confess she's in love with him. She's not.
- Funny Foreigner: Don the karaoke machine salesman plays this role initially with Brian and Jake, before dropping the act when they start quizzing him about prices.
- Good Shepherd: Brian does charity and community work and is obviously well-loved by his flock.
- Could also apply to Jake, who is popular with his congregation and helping Brian to set up a joint Jewish-Catholic community centre.
- Hey, It's That Guy!: Lisa Cuddy is one of Jake's unsuccessful dates.
- And Arvin Sloane is the president of Jake's synagogue.
- Hot for Preacher: Averted, but see Sexy Priest trope below
- How We Got Here: 3/4 of the film is Brian recounting to Pauly how he came to end up drinking in his tavern.
- I Have No Son: Jake's mom disowns his older brother Ethan after he marries a Catholic girl.
- Although it's ultimately revealed that she's at least attempted to reconcile with Ethan, who isn't willing to accept it.
- Irishman and a Jew: Anna describes her, Brian and Jake as 'Two micks and a yid'
- Ironic Echo Cut: Used after Jake's attempt to liven up his Shabbat service by having the Harlem Gospel Choir perform 'Ein Kelokeinu'
Jake: How upset are they?
Rabbi Lewis: Let's just say they're less than thrilled.
[Cut to meeting with Larry, the president of the synagogue]
Larry: To be honest we're less than thrilled.
- Jewish Mother: Jake's mom spends a lot of time harassing Jake about his love life.
- Jews Love to Argue: A brief flashback shows Jake arguing with his father. Brian's narration implies that the argument is over Jake's decision to become a rabbi instead of entering into the family business. The argument is unheard, save for Jake's closing line:
Jake: I don't wanna listen to any of you! (throws down yarmulke and storms off)
Jake: I mean, she's like your sister, Brian, that's-
Brian: Yes, thankyou for adding depth to my confusion!
- Montages: Several.
- There's a Good Times Montage showing Brian, Jake and Anna hanging out together. Overlaps as a "Falling in Love" Montage, as it also covers Jake and Anna falling in love.
- Then there's the Drunken Montage when Brian wanders the streets drinking....
- ....and this is followed by a Sad Times Montage since the trio are now separated/not speaking to each other.
- Nice Jewish Girl: Jake is under pressure from his mother and his synagogue to find a Jewish wife. Truth in Television, as Judaism is passed down the generations through matrilineal descent. Jake's brother Ethan is disowned by his mother because he married a non-Jew.
- Power Walk: Brian and Jake, to Carlos Santana's 'Smooth'. See it for yourself.
- Scenery Porn: The entire film is a loving look at New York City.
- Secret Relationship: Anna and Jake
- Sexy Priest: Lampshaded by Anna in a conversation with Brian:
Anna: I've seen the way women look at you, even though they know you're a priest - especially when they know you're a priest!
- She Is All Grown Up: Brian and Jake's reaction when they meet Anna coming off the plane.
- The Talk: A subversion of sorts. Anna asks Brian a bunch of questions about his celibacy vow.
- Triang Relations: Of the Type 4 variety, where Anna is in a secret relationship with Jake and Brian is in love with her and unaware of the relationship.
- Two Guys and a Girl
- Victorious Childhood Friend: Anna to Jake
- What, Exactly, Is Her Job?: The audience never exactly knows what Anna's job is, other than that it's in business or management. Brian describes it as 'analysing synergies or synergising analogies'
- Workaholic: Anna, and how! She carries her cellphone with her everywhere and has it strapped to her thigh when she's on a date.