After failing to find success as a writer in New York City, Jim slinks back to his family's home in the Midwest to lick his wounds. But his visit is quickly complicated when his angst spreads to his brother, Tim, who promptly decides to drive his car straight into a tree. Under the shadow of his sibling's injurious actions, Jim strikes up an unlikely friendship with Anika, whose centered small-town wisdom gradually rubs off on him.

Will Henry is a newly single graphic novelist balancing being a parent to his young twin daughters and teaching a classroom full of college students, all the while trying to navigate the rich complexities of new love and letting go of the woman who left him.

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.

Upon hearing his wife was killed in the Iraq war, a father takes his two daughters on a road trip, all the while searching for the right time and place to tell them about their mother's fate.