Harriet, the author of her college newspaper's pseudonymous student advice column "Dear Emma", is great at telling others what to do, dispensing wisdom for the lovelorn and lonely on her Midwestern campus. Somehow, though, she can't take her own advice, especially after Keith, the guy she's dating, blows her off completely. When Harriet discovers that Keith has started seeing the beautiful and intimidating Remy, she wants to hate her. But she can't help warming to Remy, who soon writes to "Dear Emma" asking for romantic advice.
Now Harriet has the perfect opportunity to take revenge on the person who broke her heart. But as she begins to doubt her own motivations and presumably faultless guidance, she's forced to question how much she really knows about love, friendship, and well-meaning advice.