Wes is in his first relationship with a girl named Meredith, but it's at a point in which much of the chemistry has worn off. His friend Richie Hall is obsessed with a girl named Rosalind. Richie is a nice guy destined to finish last, and tragically unaware of it. Wes, at the movie's start, tells Richie that he will change his relationship with Meredith. But since he is unable to properly articulate his thoughts even to Richie, it is no surprise that, a few scenes later, when he tells Meredith that the relationship is "stagnant," he has no clue how to right the ship. His solution is to run away, which is a tactic that Wes takes in all areas of his life. Meanwhile, Richie thinks he can win Rosalind like it's done in the movies, with grand confessions of his love, and he thinks not having his own apartment is what's stopping her from liking him. He thinks the overt flirtations of Emily, Rosalind's roommate, are genuine, but perhaps they are not, and he finds himself increasingly ...