Autumn in New York follows the sexual exploits of Will Keane – New York restaurateur, infamous verging-on-50 playboy, master of the no-commitment seduction – until he runs into an unexpected dead end when he meets Charlotte Fielding. Charlotte is half Will’s age and twice his match, a 21 year-old free spirit yearning to get out and taste the excitement of adult life.

Piper Grant moves to New York for a fresh start and to find her career passion. As she bounces between different exciting temp jobs that take her all over the city, she meets Austin Edwards, an aspiring writer. While Piper’s sunny optimism is at odds with Austin’s jaded personality, the magic of the autumn season soon brings them closer together. When Piper realizes her true passion is illustration, they decide to team up on a children’s book project, and in the process, they discover the thing they’re really searching for might be each other.

With plans to leave their small town, teenage loves Annie and Ben elope. Their big city plans are halted, though, when Annie’s parents have the marriage annulled. Ben moves to New York, while Annie stays in Iowa to help her family. Fifteen years later, both engaged to their respective fiancés, the two discover that their annulment was never finalized. They reunite to make their divorce legal, but begin to reminisce about what could have been. When romantic feelings resurface, Annie and Ben must decide if their past love could be the love of their future.