Dark Chester is an anonymous and highly successful criminal. Never caught. Works alone. That is, until he met Malicious Mandy, another fellow criminal who shared the same cunning mindset and the same unbreaking streak. After the two had an accidental encounter with one another, it didn't take long before the two partnered up. Together, the pair must learn how to work as a team as they perform the biggest heist of the century. With a bit of struggle and the occasional mishap, the two learn how to work their way around these problems together, perhaps helping these two partners in crime become literal partners as well.

Magma Mandy lived a somewhat quiet life alone in her cavern. That quickly changed the moment her home was attacked, forcing her to flee into the unknown Enchanted Woods. Luckily, Wood Spirit Chester immediately stepped in to help this new cute girl he happened to come across. As the two learn more about one another and their magical lands, all seems well...or at least, in the meanwhile.

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.