Lollipop Boy is the gender-swapped version of Lollipop Girl. He made his appearance in the episode "Fionna and Cake," where he was seen in the opening theme.
Unlike Lollipop Girl, he wears square glasses. He is very tall and thin, much like Lollipop Girl, and he wears small grey shoes. His clothes are large green and brown stripes, with long sleeves.
- Because Lollipop Girl is dating Ice Cream Guy, that would mean that Lollipop Boy is dating Ice Cream Girl, but in reality, there is already an Ice Cream Girl.