New York, I Love You delves into the intimate lives of New Yorkers as they grapple with, delight in and search for love. Journey from the Diamond District in the heart of Manhattan, through Chinatown and the Upper East Side, towards the Village, into Tribeca, and Brooklyn as lovers of all ages try to find romance in the Big Apple.

Failed actor-turned-worse-high-school-drama-teacher Dana Marschz rallies his Tucson students as he conceives and stages a politically incorrect musical sequel to Shakespeare's Hamlet.

A young black woman discovers that her father was a sperm donor, and if that wasn't bad enough, he's white.

Nick cannot stop obsessing over his ex-girlfriend, Tris, until Tris' friend Norah suddenly shows interest in him at a club. Thus begins an odd night filled with ups and downs as the two keep running into Tris and her new boyfriend while searching for Norah's drunken friend, Caroline, with help from Nick's band mates. As the night winds down, the two have to figure out what they want from each other.

Brad and Kate have made something of an art form out of avoiding their families during the holidays, but this year their foolproof plan is about go bust -- big time. Stuck at the city airport after all departing flights are canceled, the couple is embarrassed to see their ruse exposed to the world by an overzealous television reporter. Now, Brad and Kate are left with precious little choice other than to swallow their pride and suffer the rounds.

On the night of her college graduation, Natalie's life splits into parallel realities after she takes a pregnancy test. What will life and love bring?

A mayoral candidate (Barbara Eden) for a California town gets romantically involved with her opponent (John Forsythe), a former cowboy star.

Matters of the heart weave themselves into a love pentagon between five actors as they rehearse for a stage play in Bucharest's historic quarter.

When an entire town in upstate New York is closed down by an unexpected snowfall, a "snow day" begins when a group of elementary school kids, led by Natalie Brandston, try to ensure that the schools stay closed by stopping a mechanical snowplow driver by trying to hijack his plow truck. Meanwhile, Natalie's big brother Hal is using this day to try to win the affections of Claire Bonner, the most popular girl in his high school, while Hal and Natalie's father Tom, a TV meteorologist, faces off against a rival meteorologist for weather coverage of the day's events.

A wealthy executive, Drew Latham (Ben Affleck) has no close relationships and becomes nostalgic for his childhood home as Christmas approaches. When he visits the house and finds another family living there, he offers the residents, Tom Valco (James Gandolfini) and his wife, Christine (Catherine O'Hara), a large sum of money to pretend they are his parents. Soon Drew tests the couple's patience, and, when their daughter, Alicia (Christina Applegate), arrives, things get increasingly tense.

Jessica, a Jewish copy editor living and working in New York City, is plagued by failed blind dates with men, and decides to answer a newspaper's personal advertisement. The advertisement has been placed by 'lesbian-curious' Helen Cooper, a thirtysomething art gallerist.

Holly is tired of moving every time her mom Jean breaks up with yet another second-rate guy. To distract her mother from her latest bad choice, Holly conceives the perfect plan for the perfect man, an imaginary secret admirer who will romance Jean and boost her self-esteem.