When nerdy Adam Sorenson (Paul Rudd), an English Literature major at Mercy, a fictitious Midwestern college, meets Evelyn Ann Thompson (Rachel Weisz), an attractive graduate art student, at the local museum where he works, his life takes an unexpected turn. Never having the best success with women, he is flattered when Evelyn shows an interest in him and, at Evelyn's suggestion, gets a new hairstyle, begins a regular exercise regimen, eats healthier foods, dresses more stylishly, acts more confident and dominant, and begins wearing contact lenses instead of his usual eyeglasses. These initial changes regarding Adam's physical appearance are well received by Adam's friend, Phillip (Frederick Weller), and Phillip's fiancee, Jenny (Gretchen Mol). Jenny takes such a liking to Adam's new physique that she makes a move on Adam and the two share a passionate kiss. It is left ambiguous as to whether or not Adam and Jenny have sex. Later, Evelyn cajoles Adam into undergoing plastic surgery to fix his misshapen nose and succeeds in persuading him to cut himself off from Phillip and Jenny, whose relationship she ruins.