A handsome, fit teenage guy is exercising in his home. Kyle (Alex Pettyfur) primps in the mirror and likes how he looks: tousled blonde hair, chiseled abs and a pretty face. He goes to school, where he is running for president of the Green Committee, just so he can put it on his resume. In his speech to the students at the Tony Buckston Academy in NYC, he says this, and, “Beautiful people get it better”, so the uglies should quit trying to fit in, and “Just embrace the suck”. Kids cheer, and he is clearly someone to be feared, and idolized at school. One student, with her white-blonde hair and dark goth looks, eyes him and leaves. His friends warn him to steer clear of the witch, Kendra (Mary Kate Olsen). He speaks to Lindy (Vanessa Hudgins), a cute, dark-haired girl, who mentions that although they have gone to school together for 3 years, this is the first time he’s ever spoken to her. He looks at her, with a bit of interest.
At home, Kyle’s dad, Rob (Peter Krause) is a famous national newscaster, and only interested in how people look; this is where Kyle has learned this shallow belief. He reminds Kyle that, “People like people who look good”. Zola (Lisa Gay Hamilton), their Jamaican housekeeper, leaves for the day, and Kyle and his dad pay no attention to her.
At school, Kendra is standing near Kyle’s campaign posters which she has defaced with lipstick and written, “Don’t embrace THIS suck” on them. It is announced that Kyle has won. Kyle mockingly invites Kendra to a party later, and she says that everyone deserves a second chance, so she agrees.
At the party, Kyle is attempting to make-up with his girlfriend, Sloan (Dakota Johnson), but she is giving him a hard time. He speaks to Lindy, who is working at the party to earn money to go on the school trip to Machu Picchu in the spring. He is intrigued with this open, honest girl and poses for a photo with her, and then snaps out of it, and returns to his shallow friends. Kendra shows up, and in front of everyone, he tells her that he was joking about asking her, and she is a fool to think he’d ever be interested in someone as unattractive as she is. She smiles, and tells him that he’d “better embrace the suck” and stares at him…he feels dizzy and has blurred vision, and stumbles outside. Kendra follows him and he calls her “Franken-skank” but she laughs. She tells him that he will stay ugly for one year, and if he can find someone to love him within that time, then he will return to his former looks. If not, he will stay that way forever. He sees his reflection, and is scared by his hideous face: he has scars, tattoos and staples all over his bald head, and arms and chest. He is ugly and scary looking.
Kyle sits in the dark at home, and asks his father why he loves him? Then he turns on the light and shows his father his face. Dad takes him to every specialist, but none can fix him. Dad pleads that Kyle would do anything, regardless of the risk, to fix his looks. Kyle looks at his dad, and sees him for what he is: a superficial man. Dad rents a brownstone outside the city and tells Kyle he can spend the year here, where no one can see him or bother him. He gets Kyle a motorcycle and leaves him with Zola. He says he is moving in, but never does, always managing to be too busy in the city to make it.
Kyle’s cover story is that he is in rehab. Kids at school wonder when he has been gone over 4 months. He stays inside the house, exercises, reads posts on the social network and gets cancellation texts from his dad again and again. There is a knock at the door, and it is Will (Neil Patrick Harris), a blind teacher that Rob has sent to be Kyle’s tutor/companion.
Kyle is changing in his solitary life. He takes the time to ask Zola about her children. She explains she has 3, ages 16, 13 and 10, back in Jamaica. She had to leave them to get a green card and work, to send money home, and misses them. She tells Kyle that as she loves her children, so must his dad love him. Kyle doubts it at this point.
The tattoo of a tree on Kyle’s arm looks ghostlyit is Halloween. Kyle rides his motorcycle into the city and goes to the school Halloween party. His face blends in with the other costumes. He overhears Sloan talking about himthat she misses him, but she is happier without him because when he was with her, it made her meaner, and she felt angry and unhappy most of the time. He sees Kendra and begs her to remove the spell, but she refuses, saying he hasn’t learned anything yet, and to remember he has 7 months left to get someone to say “I love you” to him. Kyle sees Lindy, dressed as a hippie. They talk about how romance is missing, and she is sad that no one takes the time to write real hand-written letters anymore. Kyle picks up her sunglasses and keeps them.
At home the next day, Will tells Kyle that he lost his sight suddenly at age 15. Kyle tells him of his frustration of looking so hideous, and that “Chicks don’t dig ugly guys”, to which Will asks, “How do you know?” Kyle has the photo of him and Lindy, taken at the party before he lost his looks, on his computer, and looks at it often. Kyle stops by Will’s room, to see him methodically selecting a tie by feel; he asks him why it matters since he is blind? Will tells him that he dresses for himself, and not for how others look at him.
Kyle goes out every evening, and watches Lindy in her apartment window, studying. She has the same routine: she takes a break and puts on her iPod and goes to the store and buys a coffee and a box of Jujyfruit candy, eating some as she sings on her way home. This evening, Lindy hears yelling and sees her dad run-she follows, and so does Kyle, hiding from view. Two thugs have her dad by gunpoint; he owes them money for drugs. As things are about to get rough, Kyle jumps in, and pounces on the gun-wielding thug. The gun is knocked away, and the thug knocks Lindy down the stairs. Kyle runs after her; she is unconscious, and he carries her home. In the meantime, the dad has gotten the gun and killed one of the thugs. The other thug vows to get revenge by killing Lindy. Kyle tells her father that he needs to protect her by sending her to live with him, where she can’t be traced or found, and will be safe. The dad doesn’t want to, but Kyle says to tell her that she will be staying with “the son of an old friend” until things cool off, and he reluctantly agrees.
Kyle tells Zola and Will to call him “Hunter” so Lindy won’t know that he is really Kyle. She moves in, and has had to leave school; clearly she is mad at her dad for forcing this. Kyle brings her a tray of food in her room, but he wears a ski mask to hide. He leaves a gift box at her door: it is an expensive red purse. She scoffs and leaves it. Next he tries jewelry from Bulgarisame response. Kyle asks Zola what to do, and she says to stop trying to buy her, but to think about her and what SHE likes. He does, and brings her a case of Jujyfruit candy, still in the ski maskZola laughs at the mask. Lindy asks about the mask, but he doesn’t explain. She thanks him for the candy, and he leaves, smiling and happy. He happily tells Zola, “The “thinking” thing killed!” Then he remembers their conversation at the Halloween party and begins a long-hand letter to Lindy.
Kyle gets a bunch of books and is researching how to build a green house. He remembers that Lindy was on the Green Committee, and thinks she’d like it. She likes roses, and how each color means something different, so he thinks this will help him win her over. Kyle starts building on the roof, reading “Greenhouses for Dummies” as he works.
He is watching TV one night, and Lindy comes in. His hood is up, and she still hasn’t seen his face. She asks him, “Are we ever going to meet?”, so he slowly lowers his hood. When she sees his face, she stares, but is OK, and says she’s seen worse. They watch TV together and have a good time. They find out they neither of them has a mother, and that both of them have dads that are messed up. He asks her if he wants to go to class with him, as Will is his tutor and she’d love to.
Early in the morning, Kyle bangs on Will’s door and wakes him up. He tells him he needs to act as his tutor, and also like he’s been doing it all along. And...to make him look smart in front of Lindy. Will laughs and they agree on modern poetry for the first class.
Kyle takes her up to the roofthe greenhouse is completed and full of roses of every color and size. She is amazed and loves it. Will and Zola come up for class, and Lindy knows the poem Kyle selected. As the two recite it together, Zola takes Will, and they smile as they leave the two alone together. Months go by, and we see the seasons change in the greenhouse, and Kyle and Lindy meet there and talk and read poems every day. Soon it is spring, and the tree tattoo on Kyle’s arm sprouts a white rose. He knows he is running out of time.
Kyle goes to find Kendra, and begs her for more time. She tells him that magic cannot be undone or altered, and he doesn’t have much time. He asks her to at least help Zola get her kids and for Will to get his sight. She marvels that he seems to have changed for the better. She tells him she will help them, IF he succeeds.
Kyle sees the same picture of them at the party on Lindy’s computer screen. She tells him it was a jerk she knew from school, but that she thought that deep down, there was something good in his heart, and that she had kind of fallen for him.
Will suggests that Kyle take Lindy to his dad’s lake house to ratchet up the romance. They arrive-it is a huge tudor-mansion on the lake. They walk around and Kyle is about to kiss her when Lindy gets a call: her father has OD’ed and she has to go right away. He drives her to the train, and hands her all the letters he has written her, tied up in a bundle with a ribbon. As she leaves, she turns, pauses, not knowing what to say, and says, “You’re a really good friend”. Kyle is devastatedhe is just a friend to her. She reads the letters as the train pulls away.
Lindy tries calling Kyle, and leaves messages, but he won’t answer. Zola and Will tell him that she has called them, asking what is wrong. The both jump on him, to CALL HER. He sees it is the day the school is leaving for the Machu Picchu trip, and he goes there. Kids stare at him, but he doesn’t care-he sees Lindy and calls to her. She comes to talk to him, and he tells her how sorry he was that he didn’t call. He says that after she called him a friend, he was afraid that she didn’t love him, and couldn’t because of how he looked. Then he realized that he should have known better about her, and came as fast as he could. Kyle tells her to go, and that he will be there when she returns, and nothing will change (he means his face, as he is out of time). She takes off his hood, holds his cheek in her hand and kisses him. Then she starts for the bus, and turns and says, “I love you” with a smile, and leaves.
Kyle feels dizzy, and his vision is blurry. He stumbles outside and sees his reflection in the glass, and then he sees Kendra in the reflection. Soon, he is changed back to his real face. He can’t believe it! Before he can think, Lindy comes out of the school, calling for Hunter (Kyle). He stops her, and she is surprised to see long-lost Kyle. He talks to her, and asks if she can see the change in him, and the more he speaks, she realizes it is Hunter, that Hunter is/was Kyle all along. She smiles, and he comes close, hold her face in his hands, and they kiss.
Zola gets Permanent Resident visas in the mail for her children, and Will gets his sight back. They are thrilled and shocked at their good fortune.
Kyle’s dad, Rob, is at work when the secretary announces the new intern that he is getting is here. She warns him though, that she is known to be a bit difficult, and then we see tall, dark stilettos enter his office: it is Kendra.
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