Her immediate family consists of her mother Nell, a high-achieving lawyer and later judge, her father Victor, a teacher with a gentle nature, her older sister Jessica, who suffers with cystic acne and the discrimination that comes with it, and her older brother Charles, who was expelled from boarding school and makes their lives a misery.

Rachel feels Charles gets all the attention in her family, even if it is negative, and that he is driving their parents to the breaking point.

In the book, Rachel has to deal with her crush on Charles's tutor, Paul Medeiros (who ends up dating their cousin Tarren), her worries that Stephanie and Alison prefer each other to her, her frequent invitations to join high-achieving school societies, and the fact that the best-looking boy in ninth grade (at least, to Stephanie, Alison, and Rachel), Jeremy "Dragon" Kravitz, may be interested in her.

The novel's title is a reference to the Simon and Garfunkel song "Mrs. Robinson"; specifically the lines: Judy Blume has stated on her website that she "had a terrible time coming up with a title for Rachel's story and I'm not happy with the one I finally chose which comes from a line in the book spoken angrily by Charles".

Publishers Weekly and Kirkus Reviews praised the character dynamics and dialogue as "complex" yet "credible.