Jimmy is a stereotypical geek who works at the library in Oakland, California, and is trapped in his own torpidity. Sara is his best friend, but she wants to get a life (translation: an apartment in Brooklyn and a publishing internship). When Sara moves to New York City, Jimmy is rattled. Then lonely. Then desperate. He screws up his courage, writes Sara a letter about his true feelings, and asks her to meet him at the top of the Empire State Building (a nod to their ongoing debate about Sleepless in Seattle).