A modern-day take on the "Beauty and the Beast" tale where a New York teen is transformed into a hideous monster in order to find true love.
At the Buckeston Academy High School, the wealthy, arrogant, narcissistic, and bigoted Kyle Kingson is a student who does not respect his classmates. When Kyle is elected representative of the students, he plays a prank on the outcast Kendra, who has a reputation as a witch: he invites her to a party and humiliates her in front of their classmates. However, Kendra curses him with a spell that makes Kyle as ugly as his soul. Further, she tells him that if he does not find anyone who loves him within a year, he will be doomed to that appearance forever. When Kyle's father, Rob Kingson, sees him, he takes Kyle to specialists but the doctors do not know what to do, so Rob hides Kyle in an apartment with a maid and a blind tutor. When Kyle sees his mate Lindy on the streets, he saves her from a dangerous drug dealer and he brings her to his apartment to protect her. Now his only hope is that Lindy will fall in love with him.
A chip off the not-so-old or modest block, Kyle Kingson is a high school senior at prestigious Buckston Academy High School in New York City. He knows that he is wealthy and good-looking, and, based on the tenets of Rob Kingson, his wealthy, good-looking and self-absorbed news anchor father, Kyle believes those traits get one everything in life. Smug Kyle treats poorly and with disdain those who are unattractive or different. Although Kyle is generally idolized by his classmates, there are the few who want to see him brought down a notch or three because of his vainglorious attitude, and chief amongst them is Kendra. After a prank Kyle perpetrates on her--one that she saw coming a mile away--Kendra, a sorceress, places a spell on Kyle, disfiguring his face. The spell will be broken if someone can truly tell him that she loves him. If no one does so within a year, the disfigurement will be permanent. As Rob implies that he would rather have a dead son than an ugly son, he places Kyle in hiding, with only their housekeeper, Jamaican immigrant Zola Davies (who Kyle previously also treated poorly), and a tutor, a blind man named Will, in the house with Kyle. Kyle quickly changes his attitude because of his situation. He can see that he loves Lindy, a classmate to whom he never paid any attention in three years of going to the same school. She, self-described as more substance over style, is smart but from the proverbial wrong side of the tracks, and trying to get away from the troubled life with her drug-addicted father. More than anything, Kyle wants to be her protector, especially from that life. Teaching Kyle to know how to act around someone like Lindy may be a little more difficult than changing his attitude, but he requires and accepts the help of the more insightful Zola and Will. Regardless, Kyle still has to overcome his physical appearance, which he cannot do before someone (Lindy, he hopes) tells him that she truly loves him for who he is inside.
Kyle (Alex Pettyfer) thinks he is God's gift at his high school. He plays a prank on a fellow student, Kendra (Mary-Kate Olsen) who, unbeknown to him, is a witch. Kendra teaches him a lesson by putting a curse on him to make him as beastly on the outside as he is on the inside. He has one year to find someone to fall in love with him or stay like that forever.
Kyle is a rich, spoiled teen who thinks the world is at his finger tips. When a student, Kendra, calls him a jerk, he decides to play a prank on her. She retaliates by placing a curse on him that turns him into something hideous. She tells him that if at the end of a year, he can't find someone to say "I love you" to him, he will remain like that forever. He then goes into seclusion with a maid and a blind tutor. They convince him to go out and find someone. He goes out and runs into Lindy, another student at his school who is not completely turned off by his swagger. When she gets into trouble, he offers to take her in until the trouble is over. He then adopts the name Hunter and he tries to win her heart but she's not like the other girls who are wooed by his wealth.
- Kyle Kingson (Alex Pettyfer) is the arrogant and vain son of wealthy and equally as arrogant and vain news anchor Rob Kingston (Peter Krause). When he wins student body president, he bullies the eccentric Kendra Hilferty (Mary-Kate Olsen) for being ugly and strange at the after-party. Disgusted, Kendra magically transforms Kyle into a bald, tattooed and scarred shell of his once-handsome self. Kendra says Kyle has until the next spring to find someone who loves him or he stays this way forever. Rob takes Kyle to live in a private condo with their maid, Zola (Lisa Gay Hamilton), and Kyle's blind tutor, Will Fratalli (Neil Patrick Harris). Rob initially promises to support his son, but gradually neglects his son over time and stops visiting him after work altogether. Angry and hurt, Kyle finds sympathy from Will and Zola.
As spring draws closer, Kyle finds himself infatuated with Lindy Taylor (Vanessa Hudgens), a girl from his former school who he had initially been as distant to as he was to Kendra. When Lindy and her father are about to be mugged by two brothers on the street, Lindy's father shoots one of the brothers, the surviving one vowing vengeance by taking Lindy's life. Kyle saves Lindy and her father, and arranges for Lindy to move in with him for her own safety. Initially, Lindy is furious about hiding, since she was to go to Machu Picchu on a field trip - but after she claims she's seen worse when Kyle reveals himself to her (now calling himself "Hunter" around her), they warm up to each other. Kyle writes a letter to Lindy professing his love to her, but he never plans to give it to her, in fear of Lindy not feeling the same way. Will and Zola continue to help Kyle win her over, as the two begin to fall in love. In time, he completely wins her over when they read Frank O'Hara's poem "Having a Coke with You" together out loud. Closer to spring, Kyle makes a deal with Kendra that if he succeeds in winning Lindy's heart, she will restore Will's vision and grant citizenship to Zola's three children in Jamaica.
Lindy receives a text message from her father that the criminal who threatened her life is in jail. She and Kyle spend an afternoon at one of Rob's private cottages on a lake. As they are about to kiss, Lindy receives a call notifying her that her father overdosed and is in a hospital. She leaves to see her father, and Kyle gives her his letter, but regrets doing so when she tells him he's a good friend before leaving. Heartbroken, Kyle does not answer Lindy's phone calls, after she reads his letter. Inspired by Will and Zola, Kyle goes to meet Lindy one last time before she leaves for Machu Picchu, and explains he did not answer her calls because he thought she only liked him as a friend. Lindy professes her love, and departs for Machu Picchu. Kyle's normal, handsome self is restored with Kendra's spell broken, but Lindy decides against leaving and tries to find "Hunter" again. She initially ignores Kyle while searching for Hunter, only for Kyle's phone to ring when she calls "Hunter". Realizing Hunter was Kyle, the two share a kiss in the street.
Will wakes up one morning and to his delight can see again. Zola finds three green cards for her children in the mail from the government. Kendra is also seen approaching Rob Kingson's office as a new intern, implying that Kendra will likely do the same thing to Rob as she did to Kyle. In the credits, a series of photographs show that Kyle and Lindy went around the world together - including Machu Picchu.