In one of many Randal and his best friend Matt nights of unbridled revelry, Matt confesses Randal he wants to propose to his girlfriend Sally. However, the next day Randal wakes up with his friend's wallet in his pocket and with his engagement ring inside. As our hero is running short of funds, he decides to sell the ring for a large sum of money. These action unleashes a curse that will repeat that Monday again and again, until he gets to solve the conflict that he created.

Randal's Monday is a point-and-click adventure game, featuring cynical humor and geek culture references, including a hateful main character and puzzles with illogical solutions.