Isabelle "Izzy" Grossman (Irving) spends her time going from her tiny, solitary West Side apartment to that of her grandmother (Bozyk) on the Lower East Side. In between, Izzy builds a glowing reputation at the swank bookstore where she works. While her grandmother plots to find her a romantic match, Izzy is courted by a married, worldly author, Anton (Krabbe), yet can't seem to shake the down-to-earth appeal of Sam (Riegert), a pickle vendor.
Crossing Delancey provides examples of:
- An Aesop: Don't be too shallow about a person's status, they might be the perfect choice for you.
- Cute Bookworm: Izzy is a rather attractive book publisher.
- Deadpan Snarker: Izzy has a witty banter, especially around Ida.
- Sam gets a few witty lines too.
- Defrosting Ice Queen: Izzy starts off as cold and snooty towards Sam as she sees him as low-class, but she later falls in love with him when she realizes how perfect he is for her.
- Hard Truth Aesop:
- From Izzy's perspective: if you try to be an independent-minded modern woman who can make her own decisions on life and love, maybe you shouldn't — your meddling elders may be right after all and you really should be with the nice Jewish guy they pick out, even if he's a lowly, seemingly boring pickle-seller.
- From Sam's perspective: if you're a really nice guy who's genuinely interested in the woman you've been introduced to, be prepared to be dragged though the dirt and feel like a complete schmuck before you can finally end up with her.
- It's All About Me: Izzy is rather self-absorbed and a snob as she doesn't listen to Bubbe when she tries to hook her up with Sam, and believes her job is more important than her love life, she eventually learns from this and tries to make things right with Sam.
- Jerkass: Anton is revealed to be one as he only cares about having a partner as a sex assistant rather than start a relationship with Izzy. Izzy even calls Anton an "asshole".
- Jerk with a Heart of Gold: Izzy starts off as snobbish, selfish, and deceitful as she wasn't interested in Sam and was more interested in Anton and sets Sam up with her friend Marilyn, but she starts to believe Ida was right and starts a relationship with Sam.
- The Matchmaker: Bubbe serves as one to Izzy and Sam as she tries to make them in a relationship.
- My God, What Have I Done?: Izzy realizes how snobby and mean she was to Sam and tries to make it up to him
- Nice Guy: Sam is shown to be kind-hearted, as lampshaded by Izzy.
- Marilyn is shown to be funny, honest, and direct, said verbatim by Sam himself, unlike Izzy.
- Precision F-Strike: Izzy calls Anton an "asshole" as she was getting into a taxi.
- Single Woman Seeks Good Man: Izzy soon realizes how much of a Nice Guy Sam is and begins a relationship with him.
- What the Hell, Hero?: Sam calls out Izzy for setting him up with Marilyn and how she sees his life as small and defines him.
