Garrett (Justin Long) has always had a problem with commitment and understanding what women want. He seems to be doing everything right until he learns the hard way that he cannot speak the female language when his girlfriend drops him. That night, his friends want to brighten up his spirits by taking him to a bar. He meets Erin (Drew Barrymore) playing a game and ends up buying her a beer, then winning at bar trivia, and having breakfast with her the next morning. Erin is only in New York City for the summer, and will be returning to grad school in San Francisco in six weeks. They start a no-strings-attached summer fling relationship that turns into a seriously meaningful love affair. They realized that they were meant for each other, but when Erin returns home, will their love survive the distance, between New York City and San Francisco?