Not So Pure and Simple follows 17-year-old protagonist Del Rainey, a high school student who inadvertently joins a purity pledge class at his church but realizes the group gives him a chance to get close to his longtime crush, Kiera Westing. Kiera, who has had a series of long-term boyfriends, is finally single, and Del hopes to earn her love at last. However, as Del navigates the group’s meetings and the high school social scene, he confronts his own misconceptions about women, relationships, and what it means to be a “real man.”

This study guide refers to the 2020 Kindle ebook edition published by HarperTeen.

Content Warning: The source material features discussions of sexuality and sexual health; themes related to peer pressure and societal expectations; mild language and situations related to teen relationships; sexual assault; and suicidal ideation.

Plot Summary

Del Rainey, a 17-year-old junior, is excited that gorgeous Kiera Westing, his lifelong crush, is finally single. Kiera has had a series of boyfriends since sixth grade, so Del sees his opportunity. At their church’s Sunday service, Kiera walks up front with other teens, so Del follows. Because he wasn’t paying attention, he didn’t realize those going to the front were volunteering to join a sexual purity pledge class.

At school, Del attends the sex education class called Healthy Living, taught by his favorite teacher Mister Jay (MJ), who also teaches English. Because he’s in this class and Purity Pledge, Del gets conflicting ideas about sexuality, safe sex, and relationships.

Before the first Purity Pledge class, Kiera confronts Del; she says he has a reputation for being a womanizer like his best friend Qwan. Del wants to tell her that he lied; Del and his friend Shianne made up a story that they had sex a few years ago at an “orgy,” but he’s really a virgin. Del defends that you can make a commitment to change at any time. He assumes all other pledgers, like Kiera, are virgins too.

Though he tries to get to know Kiera better, she’s distant and quiet after breaking up with Colossus. Jameer, Keira’s next-door neighbor and close friend, makes a deal with Del: Del will ask Jameer’s sex-related questions in Healthy Living, and Jameer will help him get together with Kiera. Del agrees, first asking Jameer’s question about wet dreams to MJ. Del takes notes and brings the answers to Jameer.

Through multiple events at the purity classes and church, Del tries to get close to Kiera. Every time, he’s interrupted—such as meeting Kiera at a restaurant to plan their purity project but having Colossus interrupt, begging for Kiera back. Del also continues to lie; he says Pastor Newsome wants him and Kiera to lead them in their final purity project. He also lies that he’s religious like her, though he didn’t have a Bible before. When he tries to kiss Kiera one night, she steps back and says she just wants to be friends.

Cressie, Del’s older sister, returns from college for a project on sociology about women’s rights. Cressie came to interview Taylor, one of the nine girls at their high school who got pregnant the prior year. Taylor recently posted a video stating Colossus is her father’s child and isn’t sharing parental responsibility. Kiera is crushed about the Colossus news. Cressie wants to introduce Del to feminism and shows him her growing YouTube channel FemFam. Del isn’t interested, though Cressie gives him a flyer for Jaylan Talks, a super famous YouTuber who speaks about topics such as women’s rights and sex. Jaylan is coming to Cressie’s university soon.

As Del gets to know Jameer, he learns Jameer’s parents are extremely strict. They even took the door off Jameer’s room. His parents are very conservative. They don’t accept that Jameer is gay and make him confess his sins in front of the whole church, the way Pastor Newsome enforces. Kiera’s parents are similar. Therefore, Del and Kiera make plans to see Jaylan’s talk and then host a panel with the opposite information as their purity project—but they lie to their parents about meeting at the library to plan and study.

On the trip to Jaylan’s talk, Qwan admits Angie might be pregnant since they don’t always use protection. Del supports him, especially because Qwan admits he loves Angie, the only girl he’s ever spent more than a few days with.

They listen to Jaylan’s talk about topics from mental health to safe sex to being yourself and not settling in relationships. Jaylan fights for women’s rights and equality, along with sex ed, because she believes knowledge is power. Sister Vanessa, their Purity Pledge teacher, is at the event. So they aren’t caught, the Pledgers rush out of the event.

After the event, Pastor Newsome gives a sermon pointed at Del, whom he says corrupted the other children by taking them to Jaylan’s talk. They all assume Sister Vanessa snitched on them, though Jameer says later he did. Del endures the shame, as well as Kiera hanging out with a boy named Mason from their school.

One day, Mason brags about how he and Kiera had sex. Del gets in a fight with him over this slander. He tells Kiera how Mason was acting, pushing her to answer if she had sex with him. She did. Del is distraught that she broke their pledge. Kiera admits she was sleeping with Colossus, and things progressed with Mason. She lashed out at Del for his sexual past when she was guilty. Del and Kiera get in a huge fight over her choices.

With Del upset for weeks, his family hosts an “enlightened” meeting. Cressie shows him an episode of her channel; she describes how a guy sexually assaulted her during her first week of college. She explains women’s rights and how toxic masculinity is hurting people. Cressie advises Del to let Kiera go, rather than force something. Del takes offense since he’s not like her attacker. His family doesn’t think he is, but they want him to learn and grow.

Over the next few weeks, Del realizes Kiera won’t ever feel the same about him. He plans to confess his sins, make amends with everyone, and lets Cressie interview him. In the episode, Del confesses he’s a virgin who is anxious about sex and how he lied and schemed to get a girl he misjudged. He was wrong to put his ideas and judgements on this girl, and never meant to be a toxic male treating her like a prize. With Del’s confession, he wants everyone to attend church with Pastor Newsome, which helps him convince Newsome to end public shaming confessions.

In the end, Del attends prom with a friend. Kiera dances with a new boyfriend, and Qwan is with Angie, who was not pregnant after all. Del sees Mya, a friend and coworker he connects well with, in a beautiful dress. Mya is the purest girl he’s ever met and dances with her as a changed, aware, and respectful young man.