In "Raymond's Run," a girl named Gretchen P. Lewis challenges Squeaky in the May Day races. At first, Squeaky feels competitive towards Gretchen, as Gretchen is going around telling everyone she is going to win the race. In turn, Squeaky makes fun of Gretchen's freckles. Before the race, the girls don't even smile at each other in a real way because, as Squeaky says, "girls never really smile at each other." She says there is no one to teach girls to smile at each other because grown-up women don't know how to smile at each other, either. Gretchen runs very close to Squeaky during the race, and they both overshoot the finish line. Both girls wonder who actually won the race. It turns out Squeaky wins, meaning Gretchen comes in second. In the end, they smile real smiles at each other out of mutual respect and admiration, and Squeaky thinks Gretchen might help her coach her brother, Raymond, in running.