“One of the worst parts about someone dying is thinking back to all those times you didn’t ask the right questions, all those times you stupidly assumed you’d have all the time in the world. And this too: how all that time feels like not much time at all. What’s left feels like something manufactured. The overexposed ghosts of memories.”

When Mrs. Pollack assigns her class a project on “The Waste Land,” Jessie remembers reading her mother’s books of poetry. She enjoyed finding her mother’s scribbled notes in the margins and regrets never asking her about them. This lesson, that time with loved ones is uncertain, is something Theo reminds Jessie after she gets mad at her father. 

“I wish I could say I always agreed with her [...] but now I’m proud of how I was raised, even if it means I’m even more of a stranger in a strange land at this school.”

Jessie’s family was “far from poor” (32) back in Chicago, but her middle-class upbringing makes her feel especially out of place at ultra-wealthy Wood Valley. She remembers her mother valuing “experience over things,” and though this mentality isolates her even further from her peers, she is not ashamed. Despite how much she doubts herself, Jessie does know who she is and what she values, as Mrs. Pollock reminds her in Chapter 33.

“Perfect days are for people with small, realizable dreams. Or maybe for all of us, they just happen in retrospect; they’re only now perfect because they contain something irrevocably and irretrievably lost.”

Jessie remembers a game she would play with Scarlett, in which they would create their “perfect day.” Thinking back, Jessie realizes that while her mother was still alive “they all seem like perfect days” (70) and suggests that she cannot imagine ever having a perfect day again. This is her character’s starting point, and she develops a more positive mindset as the novel progresses.