Kyle Kingson, portrayed by Alex Pettyfer, is a self-absorbed and conceited heir to a wealthy family, including his equally arrogant father, Rob Kingston (Peter Krause). His life takes a drastic turn when he is elected student body president and quickly bullies the uniquely eccentric Kendra Hilferty, played by Mary-Kate Olsen, for her unconventional looks during the after-party. In a fit of disgust, Kendra casts a spell that transforms Kyle into a grotesque version of himself—bald, heavily tattooed, and scarred, a stark contrast to his former good looks. The only way he can revert to his original self is to earn genuine love from someone before the season changes to spring.
Sent away by his father to a luxurious condo with only a maid named Zola (Lisa Gay Hamilton) and a blind tutor, Will Fratalli (Neil Patrick Harris), Kyle faces growing neglect from Rob as the time ticks away. Despite the heartache, he finds solace and understanding in the company of Will and Zola as he navigates his new reality. As the spring deadline approaches, Kyle finds himself drawn to the beautiful Lindy Taylor, who is played by Vanessa Hudgens. Initially, he had kept his distance from her, just as he had treated Kendra.
Their lives intertwine violently when Lindy and her father almost fall prey to two muggers; her father's desperate action leads to a deadly threat from the surviving mugger, putting their lives at risk. To protect her, Kyle brings Lindy to his home, where she initially resents the confinement that interrupts her plans to visit Machu Picchu. However, as she discovers Kyle's true identity—he now calls himself "Hunter" around her—the walls between them begin to dissolve.
Kyle pens a heartfelt letter to Lindy but struggles with the fear of rejection, keeping his emotions hidden. With the encouragement of Will and Zola, the two gradually find love, culminating in a poignant moment where they both share Frank O'Hara's poem "Having a Coke with You." As spring looms nearer, Kyle strikes a deal with Kendra: if he wins Lindy's love, she will restore Will's sight and grant Zola’s children citizenship.
Lindy receives news that the criminal is in custody, prompting a heartwarming day spent at Rob’s lake cottage. Just as they prepare to share a kiss, a call about her father’s overdose shatters the moment. Kyle gives Lindy his letter, only to heart-wrenchingly watch her leave, viewing him merely as a friend.
Distraught but inspired by Will and Zola's support, Kyle goes to offer an explanation. He reveals that he thought Lindy only saw him as a friend, but Lindy confesses her love just before flying off to Machu Picchu. After Kendra's curse is broken, Kyle regains his handsome looks, but the search for "Hunter" leads Lindy back to Kyle, culminating in a romantic street encounter where they finally share a kiss.
In a touching conclusion, Will awakens to find himself miraculously able to see, and Zola receives green cards for her children. Kendra, now an intern with Rob, hints that history may repeat itself. The credits roll as nostalgic photos reveal Kyle and Lindy exploring the world together, including her dreams at Machu Picchu.
