Oliver Jensen had no intention of colliding with Helene Lucia that rainy Monday night. However, fate had other plans. The well-educated, charming, often angry city boy meets the narcissistic, entitled, often judgemental runaway who has never settled down in her life, moving from city to city because of the pure boredom that radiates off of the cities she visits. Or so she says. But Oliver is determined to let her see the true beauty of city and that a single place could keep a girl like Helene utterly and deeply satisfied. With only a month to impress the critical and mystifying Helene, Oliver must try to convince Helene of all the great things his hometown of New York City holds, even if it means losing her to her instinct of running away.