Mandy is the young ruler of Candyland, surrounded by many of her loyal and talented subjects, who despite her loud and sometimes chaotic nature, continue to serve her without complaint. Her favorite in particular was her personal jester, Chester, who despite being highly annoying, she couldn't will to ever fire. Many question why she still keeps him, but hidden beneath all those lies are some deeper feelings she can't truly understand. However, little did she know that she would be tricked by the head of her royal knights, causing her to lose her royalty. Luckily, with her jester at her side, the two push through as he helps her regain her kingdom, all the while their shrouded emotions covered by their royal duties begin to finally blossom.

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.