Mandy and Chester are high school students, where Mandy secretly has an altar ego called the "Candy Queen", where she answers questions from students after they put slips of paper into a box labeled "Ask for Advice". One day, Mandy receives a question from a person named "Jack of All Trades", asking for advice on how to confess to someone. When she finds out that it was Chester, and that he was referring to her, she struggles on how to reveal that she knew about this the whole time.

Chester means no harm to Mandy, and only wants to have fun. But when a prank gets too intense, she lashes out and refuses to talk to him, despite wanting to. With the help of their friends, they start repairing their friendship and eventually building it into something more.