Carolyn McDuffy (Christina Ricci), in an effort to help her sorority sisters win a coveted award that has eluded them in the past years, joins them in training some handicapped young adults for the Challenged Games (a fictional version of the Special Olympics). Carolyn is linked with Jesse "Pumpkin" Romanoff (Hank Harris) and is horrified, mostly because she has never been in such an environment. Pumpkin is kind towards her and soon she finds herself falling in love with him because he is genuine, unlike her sorority sisters, as led by Julie Thurber (Marisa Coughlan), and her boyfriend, Kent Woodlands (Sam Ball).
Carolyn experiences backlash and disdain about the relationship from her friends and family, including Pumpkin's own mother, Judy (Brenda Blethyn), despite the fact that Carolyn's love has inspired Pumpkin to get out of his wheelchair and become the best athlete on the team. Judy later walks into her son's room and discovers that Carolyn and Pumpkin have been sexually involved. Pumpkin's mother accuses her of raping her son, claiming Carolyn "has no idea what she has done" to Pumpkin. Pumpkin's mother calls Carolyn's school, causing Carolyn to be kicked out of both her sorority and her school. Carolyn makes a suicide attempt by taking most of the pills and solutions from her medicine cabinet, but no real damage is done as Carolyn then throws up everything she took.
As Kent and Carolyn make the ideallistic "perfect couple," their attendance to the sorority ball would secure a win for the sorority award. The sorority pulls strings to allow Carolyn back into school and the sorority, where Kent takes her back. At the ball, Pumpkin and his friends crash the party to allow Pumpkin a dance with Carolyn. Kent won't stand for it and punches Pumpkin repeatedly as the girls hold Carolyn and keep Pumpkin's friends at bay. Kent turns his back as Pumpkin gathers his wits, charging and tackling Kent, knocking him unconscious for a few seconds. Kent gets up, looks around, and runs off crying. Carolyn tries to take Pumpkin inside to the dance, but Julie and the sorority sisters won't let them in. Carolyn pushes her way through with Pumpkin and they dance alone. Soon, others start to see the love between them and join them on the dance floor.
As they're dancing, Kent is shown driving erratically and sobbing hysterically. He swerves to avoid a truck and plunges off a cliff with the car exploding in midair, crashing to the bottom. Carolyn goes to the hospital to check on Kent and finds that he is now paraplegic, though not burned from the explosion. He blames Carolyn for his problems and she is left distraught. She quits school and the sorority, swearing off Pumpkin forever. The sorority stops helping the team and the rival sorority wins the award. Carolyn enrolls at a public university, opening up to her peers who encourage her to go for what she wants.
The sorority sisters have a change of heart and show up at the Olympic event. Kent is now the coach for Pumpkin's team and has become both a motivator and humble person. Pumpkin races his rival, a bully who berates Pumpkin at every chance given. Pumpkin is motivated by Kent, telling him to win it for Carolyn and saying she wouldn't want him to lose. As he's running, he sees Carolyn in the stands and gets a sudden boost of energy. Pumpkin wins the race, and at the finish line is congratulated by the sorority sisters, his mother, and Kent. Carolyn comes down to see Pumpkin as his mother is hugging him. She endears him to Carolyn, finally accepting her son's progress into a man. As Carolyn and Pumpkin walk off together, she asks him what name she should call him, his real name, and he replies that "Pumpkin will be fine."Christina Ricci as Carolyn McDuffy
Hank Harris as Jesse "Pumpkin" Romanoff
Brenda Blethyn as Judy Romanoff
Dominique Swain as Jeanine Kryszinsky
Marisa Coughlan as Julie Thurber
Sam Ball as Kent Woodlands
Harry J. Lennix as Robert Meary
Nina Foch as Betsy Collander
Melissa McCarthy as Cici Pinkus
Caroline Aaron as Claudia Prinsinger
Lisa Banes as Chippy McDuffy
Julio Oscar Mechoso as Dr. Frederico Cruz
Phil Reeves as Burt Wohlfert
Marisa Parker aka Marisa Petroro as Courtney Burke
Tait Smith as Hansie Prinsinger
Michael Bacall as Casey Whitner
Amy Adams as Alex
Pumpkin received mixed reviews from critics; 27 of 43 reviews compiled by Rotten Tomatoes were negative, resulting in a "Tomatometer" score of 39%. At Metacritic, the film received a metascore of 46% based on 24 reviews.
One of the most positive reviews was by Roger Ebert for the Chicago Sun-Times; he wrote, "Pumpkin is alive, and takes chances, and uses the wicked blade of satire in order to show up the complacent political correctness of other movies in its campus genre." Michael O'Sullivan of the Washington Post also approved of the film, calling it "an odd and oddly endearing romantic black comedy." On the other end of the spectrum, Todd McCarthy of Variety wrote that the film "gets along on curiosity value for a while, but becomes increasingly unconvincing and ludicrous as it staggers endlessly toward the finish line."
Pumpkin opened in American theatres on June 28, 2002 in a limited release. It grossed $30,514 in eight theatres in its first weekend, with a per-screen-average of $3,814. The film expanded to 19 theatres the following weekend, but its theatre count declined from there. Pumpkin completed its theatrical run four months later with a final gross of $308,552.
Since the film's DVD release, the film has become a cult hit. It is often recognized as one of the first examples of genre bending. Ricci herself has called it "a great movie" and Jeff Weiss of Stylus magazine called it "one of the most underrated films of the decade."