Friendship plays an interesting role in each of the characters' own personal story. For the majority of his story, Will Grayson 1 and Tiny Cooper have a scattered friendship, with visible cracks from the mistakes that Will has made in his past. As for will grayson 2 and Maura, their friendship reflects more of a touch-and-go relationship, picking up and leaving off whenever will decides to consider Maura as his friend. With the blossoming relationship between Jane and Will Grayson 1, soon Will and Tiny begin to drift apart. The role of friendship creates a series of changes, breaks, differences, and conflict throughout each of the protagonists' stories.
Music is referenced to throughout the story with Neutral Milk Hotel, a band that brings together all of the main characters in the book and becomes entangled in each of their stories. While the music groups, both real and fictional, do not become characters themselves in the story, the music that they create becomes relevant to each of their personalities. While both obscure Jane and nonchalant Will Grayson 1 both share a common interest with the alternative band Neutral Milk Hotel, Tiny Cooper, the fabulously flamboyant character of the story, fancies big, bold Broadway-showtunes and music that becomes main-streamed as iconic pop culture.