Craig is Sam’s college-aged boyfriend. He’s an art student who works as a male model, a gig that allows him to pay for his education. Craig often attends parties with Sam and her friends, taking photographs on a film camera. Charlie believes that Craig’s photographs are beautiful because the people in them, like Sam, are beautiful, not because Craig is a particularly talented photographer. Although Craig and Sam spend a lot of time together and their relationship appears to be fairly serious, Craig refuses to accompany Sam to events associated with high school, like dances, suggesting that he expects Sam to participate in sex and partying with him but is unwilling to reciprocate by showing interest in the reality of her life as a high school student. Sam is a pretty girl, and Craig’s feelings for her seem to mainly revolve around her physical beauty. He wants to possess Sam as an object – as Sam later confesses to Charlie, she was controlled in the relationship and felt pressured to tailor her life around Craig and his interests rather than her own – but doesn’t attempt to engage with her on a deeper level.

It’s difficult for Charlie to understand why Sam chooses to be with Craig when, at worst, he mistreats her, and at best, he’s an unsupportive partner. Sam was likely initially attracted to Craig’s good looks and successful life in the art world and quickly became too deep in the relationship to extract herself once Craig’s less appealing qualities became apparent. Additionally, Sam was sexually abused by her father’s friend as a child, a traumatic experience that led her to seek male approval in an unhealthy manner. The judgmental and controlling Craig triggered Sam’s need for male approval, and she settled into a familiar power dynamic. However, like many characters in The Perks of Being A Wallflower, Sam gains confidence and perspective throughout the school year. When Craig admits to having cheated on Sam with multiple women throughout their relationship, Sam is strong enough to end the relationship on the spot. Craig’s unfaithfulness confirms that he was never truly committed to or in love with Sam. Craig himself even tells Sam that she was right to break up with him, suggesting that he is aware that the relationship had an unhealthy dynamic due to his behavior. 

In many ways, Craig is Charlie’s antithesis. Where Charlie is gentle, sensitive, caring, and loyal, Craig is controlling, aloof, selfish, and unfaithful. Sam’s relationship with Craig shows that her perception of her self-worth is twisted – her abuse has taught her that being in a romantic relationship with a man means that she must make herself small and submissive in order to please him. By the end of the novel, Sam is interested in pursuing a romance with Charlie – who she knows loves her for who she really is, not just for her looks – rather than Craig, implying that she has begun to heal from her traumas and is ready to accept the kind of love she truly deserves, as Bill would say.