Dana is a small town girl, new to New York and staying in the lavish apartment of an old college roommate, Amy and her husband, David. Having moved to New York to pursue her dreams of working at a publishing house, she realizes life in the city isn't everything she thought it'd be as she deals with a few rude co-workers.
Amy decides to set Dana up with her brother in law Peter, a resident New Yorker who works alongside his family at a company that makes trophies. Although hesitant at first, the two agree to the date.
The date starts off okay, but Peter is very dismissive of Dana's New York bucket list and he fails to comfort her when she becomes upset thinking about how awful the date is going and how badly work has been. She ultimately leaves him in the restaurant.
Amy insists that Peter makes things right with Dana, so he shows up with flowers. Dana agrees to go out with again but changes her mind after hearing that he only apologized to her because Amy made him.
After some prodding from his sister and realizing that maybe there was more to Dana than he thought, Peter arrives to whisk Dana off to the Statue of Liberty so she can erase something off her bucket list.