Ronald Miller (Dempsey) is a typical high school nerd living in Tucson, Arizona. He has spent all summer mowing lawns to save up for a telescope. However, at an opportune moment he makes a deal with popular cheerleader Cindy Mancini (Peterson) to "rent" her for $1,000. She agrees so that she can afford to replace a suede outfit that Quint (Cort McGown), a baseball jock, spilled red wine on at a party. It belonged to her mother and she hadn't received permission to borrow it. Having few options except telling her mom the truth, she reluctantly agrees to help him look "cool" by pretending to be his girlfriend for a month even though she already has a boyfriend named Bobby who is away at college. Both agree never to reveal the pact.
Ronald then trades his nerdy-but-loyal friends for the shallow popular students and undergoes a complete clothing and hair makeover at Cindy's direction. Over the month the two discover each other's individuality and are drawn closely together. Cindy soon starts to genuinely like Ronald. She opens up to him as he washes her car at her house, she goes inside to get a poem that she'd written that meant the world to her and lets him read it. She gets to know him better as he opens up to her with his beliefs about astronomy and space travel; as they gaze at the moon he tells her how when they are their parents age "people will be working there and living there... maybe even us". On the last date which Ronald has "paid" for Cindy then hints that she'd like to kiss Ronald, signifying that she has real feelings for him, but he misunderstands and assumes she wants to talk about their breakup. They dramatically "break up" in front of a crowd at school but Ronald takes things too far and says some hurtful things about Cindy in front of their friends. She becomes cool and distant but warns him that popularity is hard work and he needs to make sure he "stays [him]self". The next day, Cindy appears disgusted with Ronald when she sees him behaving arrogantly at school and becomes jealous when she sees him flirting with her best friends Barbara and Patty, who he later takes out on dates.
Ronald continues playing "cool" by hanging out with the jocks and hot chicks. He takes Patty to a dance at school, where he performs a dance he learned from the African Culture channel on television which he mistakenly believed to be American Bandstand. At first the other kids are mystified but they soon join in and Ronald's new 'trendy' dancing makes him the most popular guy in school. At Halloween he and the other jocks drive to the house of one of his nerd friends, and the jocks test his loyalty by making him throw a bag of dog poop at the house as is their Halloween 'tradition'. But Ronald's friend is lying in wait and catches Ronald; he lets him go before his dad can call the police but the next day at school he ignores him.
At a New Year's Eve party Ronald gets pretty drunk, goes into the bathroom with a girl and has sex with her. Cindy walks by and hears Ronald reciting to this girl the very poem that she (Cindy) had written. She's completely devastated, so she starts drinking heavily. Later, as a surprise Bobby (Cindy's boyfriend) shows up at the party from the University of Iowa as he still has strong ties with most of the athletes. After he learns about her relationship with Ronald through a few of the athletes, Cindy is brutally dumped in front of a lot of people. In anger and frustration she tells the party-goers the truth about her relationship with Ronald and his "cool" pretenses. She scolds her friends for falling for his act and for being "a bunch of followers".
"Our little plan worked, didn't it Ronald?" Cindy says as she effectively puts him back at square one with not only the popular crowd (who now are back to teasing him and throwing food at him), but the nerdy crowd as well. He suffers much emotional distress at being socially ostracized as his attempts to reconcile with both Cindy and Kenneth are rebuffed.
However, a moment comes to redeem himself when he defends Kenneth against the onslaught of Quint. Ronald points out that they were all friends at one time. When they were nine, Quint had fallen out of their tree house and broken his arm, they carried him twelve blocks to the hospital as he cried all the way. He tells them that the cool/nerd dynamic is "all bullshit, it's tough enough just being yourself." and walks away. Quint and Kenneth shake hands and the whole school applaud.
Cindy recognizes Ronald's worth after that and they reconcile when she decides to hop on the back of his riding lawnmower instead of hanging out with her popular friends. He asks her to the prom and they kiss as the title song plays. The closing credits roll while they ride off into the sunset on the lawnmower.
- Patrick Dempsey as Ronald Miller
- Amanda Peterson as Cindy Mancini
- Courtney Gains as Kenneth Wurman
- Seth Green as Chuckie Miller
- Sharon Farrell as Mrs. Mancini
- Tina Caspary as Barbara
- Darcy DeMoss as Patty
- Cort McCown as Quint
- Eric Bruskotter as Big John
- Gerardo Mejía as Ricky
- Dennis Dugan as David Miller
- Cloyce Morrow as Judy Miller
- Devin DeVasquez as Iris
- Ami Dolenz as Fran
- William Hannah V as Telescope Salesman
The film was shot on location in Tucson, Arizona, at Tucson High Magnet School (then known as Tucson High School). The choreography is by Paula Abdul, who makes an uncredited appearance as a dancer. When the filmmakers decided to make this a non-union shoot, the Screen Actor's Guild protested the filming, going so far as to send representatives to the school to discourage students from appearing on camera. Because of this, none of the school's drama students chose to appear as extras in the film. On a date where the main characters begin to bond, they jump the perimeter wall and explore the 309th Aerospace Maintenance and Regeneration Group Aircraft Bone Yard on Davis–Monthan Air Force Base that contains 4,400 aircraft.
Although the characters say they jump the fence at 309 AMARG, "The Boneyard" the actual scene looks more like it was shot at Bob's Air Park, an aircraft recycler just outside the boneyard, which has since been sold.
Caryn James in the New York Times wrote that the film missed its mark and traded its potential originality for a bid at popularity by writing, "Michael Swerdlick, the writer, and Steve Rash, the director...waste a chance to make the much deeper, funnier movie that strains to break through. [The film]...has an identity crisis that's a mirror-image of Ronald's own. He thinks he wants popularity at any price, though he's really a sincere guy. The film thinks it wants to be sincere, when all it truly wants is to be popular, just like the other kids' movies, so it sells off its originality."
The film ranked number 41 on Entertainment Weekly's list of the 50 Best High School Movies in 2006.
Young Artist Award
- Won: Best Young Actor in a Motion Picture - Comedy, Patrick Dempsey
- Nominated: Best Young Actress in a Motion Picture - Comedy, Amanda Peterson
- Nominated: Best Young Actress in a Motion Picture - Comedy, Tina Caspary
- Nominated: Best Family Motion Picture - Comedy
- Can't Buy Me Love trailer at YouTube
- Can't Buy Me Love at Box Office Mojo
- Can't Buy Me Love at Rotten Tomatoes
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