Erica Tremblay as Izzy Kingston, Samantha's sister.

Nicholas Lea as Dan Kingston, Samantha and Izzy's father.

Sam's spirit sees Juliet standing over her body saying that Sam saved her Sam states, 'No. As she dies, Sam remembers all the good times she has had. She again intervenes to save Juliet, but when Juliet attempts to run into traffic, Sam pushes her out of the way at the last second and is killed by a truck. At the party, she kisses Kent and tells him she loves him. She sends roses to both Juliet and Kent, breaks up with Rob and tells her friends why she loves them. She resolves to be kind and considerate as she goes about her day. Sam wakes up again with a sense of calm and understanding, knowing what she must do to end the loop. Juliet commits suicide by running in front of Lindsay's car, horrifying Sam, and making her realize that it was Juliet who was hit by the car on the original day. When the two were on a camping trip and Lindsay wet her sleeping bag, she blamed Juliet and had been bullying her ever since. Sam tries to apologize and learns from Juliet that Lindsay's misery from her parents' fighting and divorce caused her to start wetting her bed. She hears the fight between Lindsay and Juliet from the hall and chases after her through the woods. In another loop, at the party, Sam and Kent remember their earlier friendship, with Kent recalling how she had heroically defended him from a bully after his father died and that he had resolved to one day be her hero. During these loops, she attempts to make amends with Anna Cartullo, a student she had bullied and becomes closer to Kent, who comforts her after an unsatisfying first sexual experience with Rob. Realizing that nothing she does matters, she starts doing whatever she wants, first airing her grievances with everyone she knows, then trying to spend more quality time with the ones she loves. Even though Sam manages to avoid the crash, she continues to live through the same day over and over again. They avoid the crash, but find out later in the night that Juliet committed suicide, with Sam also discovering that Lindsay and Juliet were once best friends. Realizing she is in a time loop, she convinces the group to have a sleepover instead of going to the party. Thinking the previous day was just a nightmare, Sam continues on with her day but finds that the similar events occur, and they again crash after leaving the party, though slightly later. Sam wakes in her room on Cupid's Day again. As Sam and her friends are driving back from the party, the car hits something and crashes, apparently killing them. Lindsay confronts her and the two fight, resulting in many of the guests dousing her with beer.

During lunch the girls make fun of Juliet Sykes, an outsider girl who they view as a 'psycho'. Kent invites her to a party at his house, but she is unenthusiastic. During a class lecture on Sisyphus, students distribute roses, with Sam getting one from Rob and another from a boy named Kent McFuller, a former grade school friend who is in love with her. She is picked up by her friends, queen bee Lindsay, Ally and Elody, who are excited about Sam's plans to lose her virginity to her boyfriend Rob that night.

Samantha Kingston wakes on February 12, known as Cupid's Day.

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