Middle school is often difficult for any student; navigating the social waters while exploring personal identity is tricky. At the start of Lily and Dunkin, both protagonists suffer anxiety regarding how they will fit in during middle school. Lily knows that she is “Lily Jo McGrother. Girl” (9); however, part of her is terrified of how others will respond. Her father’s disapproval and the bullying that she experiences at the hands of Vasquez and the Neanderthals make her hesitate to be her true self in a visible manner. Additionally, Lily wishes to pursue a friendship with the new boy, Dunkin. In doing so, she believes that she must change herself, opting to cut her hair to evade Vasquez’s ire and give her relationship with Dunkin a chance.

Dunkin also changes himself to gain social acceptance. From the start of the novel, Dunkin plans to go by a different name, feeling that Norbert will not win him any points in the popularity department. When he first meets Tim, Dunkin feels instantly connected to him, but Dunkin rejects Tim after the popular jocks offer acceptance. Dunkin watches as the Neanderthals bully Tim, but he walks away or stays quiet, fearful they will train their sights on him or reject him from their group.