Hailey Grant is one of Starr’s two closest friends at Williamson. At the beginning of the novel, Hailey and Starr’s friendship is on shaky ground because Hailey unfollows Starr’s Tumblr after Starr begins posting about Black issues. This seemingly small incident highlights a major complication in the relationship between Hailey and Starr. Starr cannot bring aspects of her life in Garden Heights to Williamson Prep, and Hailey is not allowed to visit Starr in Garden Heights. Therefore, by unfollowing Starr’s Tumblr, Hailey has effectively communicated that she prefers when she doesn’t have to think about the racism that affects Starr’s life. Hailey’s discomfort with race becomes even more evident as the novel progresses. Her laser-focus on Khalil’s drug dealing as justification for his murder serves as a protective measure that keeps her from having to question the system she lives in. If Khalil’s death was justified, she does not need to question the goodness of law enforcement, the fact that she’s not allowed to visit Starr’s house, or why Starr re-blogging Emmett Till’s story makes her feel so uncomfortable.

Throughout the novel, Hailey acts as a symbol of white privilege in the way she expects the people around her to always center her feelings and experiences. As Lisa observes, Hailey treats Starr and Maya like the supporting cast in her life. For example, when the trio decide they want to start a band, Hailey insists on playing lead guitar, leaving Starr as the drummer, a less prominent role. Her need to be the most important in the group informs how she treats Starr during their conflicts. Every time Starr calls Hailey out on her racist remarks, the only thing Hailey focuses on is that she doesn’t like being called racist, prioritizing her hurt pride over Starr’s grief. She refuses to consider Starr’s experience instead of privileging her own. At the end, Hailey expresses a desire for her friendship with Starr to return to the way it was. Because their previous friendship dynamic consisted of Hailey being the constant emotional center of the group, what Hailey really means is that she wants to return to a time where her friends never challenged her, something both Starr and Maya have outgrown in favor of staying true to themselves.