Plot

Three ex-girlfriends of a serial cheater set up their former lover to fall for the new girl in town so they can watch him get his heart broken.

Kate (Brittany Snow) is the new girl in school. She catches John Tucker (Jesse Metcalfe) dating three different girls at once: Carrie - the smart girl, Heather - the cheerleader, and Beth - the activist slut; none of them are aware that they are not the only girl in John's heart. Kate, having been raised by a single mother, has seen the pain caused by playboys like John Tucker, and she won't stand idly by. Together with the three jilted ex-girlfriends, they hatch a plan to teach John a lesson. Things rarely go as planned, especially when Kate starts to think that she might be falling for John herself.—napierslogs

Teenager Kate Spencer has always felt invisible to the world, largely living in the shadow of her beautiful divorced mother, Lori Spencer, who catches the attention of every man she meets. Kate has collectively nicknamed all Lori's boyfriends "Skip", as they always skip out on her, Lori who picks up and moves in the aftermath. In moving to Portland, Oregon, Kate's invisible status changes out of circumstance. She gets drawn into a school crowd consisting of media expert Carrie Schaeffer, head cheerleader Heather Straham, and sexually active activist Beth McIntyre, the three who did not travel in the same social circle until Kate's arrival. Their common bond is popular John Tucker, the school's star basketball player and big man on campus. The three learn that John has been dating each of them behind the other two's backs, telling each that they are "the one". This revelation brings out the claws in each of the three who attack the other two. However, Kate, in her experiences with the Skips, convinces them that the other two are not the enemy, but John himself, who has played each of them, making them feel like the guilty party instead of him. So Kate convinces them that the best course of action is for the three of them to bond together to get their revenge against John. Being too close to the subject, the three believe they need Kate's help. Their plan is to transform Kate into the perfect girl - an amalgam of the three of them - to catch John's wandering eye, after which she will dump him and break his heart. There are several potential problems in their plan. John's popularity may make him immune to any backlash against him that they may try to cause. Inexperienced Kate, who has never had a boyfriend, may not only not be equipped to navigate dating, but she may fall under John's spell despite she having seen the slime-ball in him in action. And Kate being involved with John may jeopardize any possibility of a relationship with who she seems to be mutually attracted, namely John's younger brother, Scott Tucker, who, like Kate, has largely lived in the shadow of his more popular relative.—Huggo

Kate Spencer (Brittany Snow) is a teenage girl who lives with her single mother, Lori (Jenny McCarthy) (who is much hotter than Kate), whose poor taste in men causes them to move around frequently. Kate and her mother move to a suburb of Portland, Oregon, where Kate gets a job as a waitress. While at work, she sees popular local boy John Tucker (Jesse Metcalfe) on dates with three different girls: chronic overachiever Carrie (Arielle Kebbel) (who is writing a children's book and is the school journalist), head cheerleader Heather (Ashanti), and promiscuous and liberal vegan activist Beth (Sophia Bush). Kate has a crush on John herself. Kate learns from a co-worker that John dates girls from different cliques at his school so that they never interact. John convinces the girls to keep their relationships secret by claiming his father forbids him to date during basketball season.

One day in gym class, Kate, Carrie, Heather, and Beth end up on the same team for a volleyball game. During the game, Carrie brags about her secret relationship with John Tucker, and the girls learn about his scheme. Carrie, Heather and Beth begin fighting. Kate tries to intervene, only to get all four of them sent to detention. Later that evening, the girls enlist Kate's help in seeking revenge against John. Meanwhile, Kate becomes friends with John's brother Scott (Penn Badgley), better known as "The Other Tucker". Scott is nice to girls, and unlike John as much as one can be. The girls make several attempts to bring John down, including a PSA campaign claiming he has genital herpes (He gets a teen responsibility award for modeling for the campaign) and mixing estrogen into his protein powder (he gets super sensitive, but the ladies love it), but these initial pranks backfire as John manages to use them to his advantage. John breaks up with all three girls, and they agree that breaking his heart is the ideal revenge. They enlist Kate to be the heart-breaker.

Scott asks Kate to be his lab partner. Armed with the girls' advice on how to impress John and a fresh makeover, Kate joins the cheer-leading squad to get John's attention. He immediately notices her and tries to flirt with her, but Kate dismisses him. John is dismayed that a girl is impervious to his charms, being shy, and becomes determined to win her affections. He asks Scott for tips to impress Kate.

John invites Kate on a date to a bonfire at the beach, while Carrie, Heather, and Beth keep an eye on things using a surveillance camera hidden in Kate's bra. Scott is thrown back to see Kate dating John at the beach. Kate is unprepared after John offers to drive her home, and Beth intervenes to teach her how to kiss. John arrives, forcing Beth to hide in the back of his Land Rover. At her house, Kate buys Beth time to escape by kissing John, but Beth's skirt gets caught in the car door and ripped off in the process. John relentlessly chases after Kate, even driving by her house, much to the girls' amusement as they watch him fall for her.

The next date is a romantic boat ride, and Kate and John have a good time together. Beth later notices that Kate is falling for John. To counteract this, Carrie secretly videotapes John bragging to his friends in the locker room, saying he'll be scoring "more than baskets" at the upcoming away game. Upon seeing John's chauvinistic behavior, Kate snaps out of it and recommits to the plan.

The girls try another plan to embarrass John at a hotel on the night of the away game. Kate seduces John on a video-chat, instructing him to put on a lacy thong and climb out of his room and into hers. He mistakenly climbs into a teacher's room instead and becomes the laughingstock of the school. John again uses this to his advantage, convincing the boys on his team that the thong is a fashion statement that improves his game. Meanwhile, Kate's mother and Scott both discover the plan and lament the change in Kate's behavior.

Afterward, Kate tells John that she heard about what he said in the locker room. John makes amends by giving her his watch and asking her to be his girlfriend. Kate tells Heather, Carrie, and Beth that she wants to be out of the plan, as whether they are dating or plotting to destroy John Tucker, it is still all about him. At John's birthday, the tape the girls made of John's destruction is played, and Kate reveals the entire plot as John is devastated. Heather, Beth, and Carrie defend her after a guest throws his drink at Kate. Still, John Tucker becomes unfazed, and the party devolves into a cake fight. A few days later, John and Kate agree to be friends, and John resolves to be honest. Scott, happy that Kate confessed, becomes her lab partner again, and it is hinted the two will begin dating. Kate is now good friends with Beth, Carrie, and Heather. Kate finishes saying, "as for the girl who made John Tucker fall in love, well, she's a legend". After the credits, Kate warns viewers at home wanting to try this that destroying a man has consequences, and the camera pans to several male teachers bending over to grab some papers, all wearing thongs.