Book details
Sheri Cobb South - Author
Penny’s plan to steal a basketball playbook is tied to both a sorority initiation and her wish to impress Brandon. Her growing feelings for Woody complicate the betrayal she has agreed to carry out.
To pass her initiation into Pressler High's most exclusive sorority, Penny Collier must steal a rival school's basketball playbook. Though she's not crazy about the idea, she is crazy about basketball star Brandon Phillips. Hoping to impress Brandon, she agrees to filch the playbook from her friend Woody, a member of the rival team. Though she feels guilty, Penny convinces herself that it's just a harmless prank. But as she gets to know Woody better, Penny realizes that she's falling in love with him. How can she bring herself to steal from the boy who has stolen her heart?
Book Analysis
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Sign in for personalised guidanceHow the book presents it: Penny feels guilty but tries to regard the act as harmless, placing her reasoning alongside the risk to a friendship.
Talk about: How does Penny’s view of the plan compare with what loyalty to a friend might require?
Talk about: If Penny’s feelings change, how might that affect the way she thinks about her agreement?
The story sets social acceptance and romantic hopes against Penny’s guilt and friendship with Woody, making her judgement about what counts as harmless a central tension.
Penny plans a dishonest act against a friend and initially persuades herself it is harmless. This may be worth noting if peer pressure or breaches of trust are sensitive topics for your reader.
What makes Penny call the plan harmless, and what might help her weigh the initiation against her friendship with Woody?
Read together in short stretches and pause when Penny’s reasons shift. Invite your reader to consider how her choices affect trust, without assuming the story’s ending or judgement.
Theme indicators describe how the book presents a topic; they are not a verdict on the whole book or your family's values. Confidence reflects how much book-specific material was checked. Only part of the book information was available, so some details remain unconfirmed.
That Certain Feeling - Sheri Cobb South - Google Books
Limited information
Checked: 1 October 2026.
Relevant to: Peer pressure and trust
That certain feeling by Sheri Cobb South | Open Library
Limited information
Checked: 1 October 2026.
Relevant to: Romantic conflict
Benefits, discussion questions and reading approaches are suggestions. Your knowledge of your child remains part of the decision.
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