Peter Parker has severe depression since Tony Stark's death. He harms himself and can't seem to find happiness anymore. Meanwhile, Y/N Y/L/N's family has been through some financial changes, and she'll do anything to get some money. When Flash Thompson suggests a game to see who can make the biggest loser in school fall in love with them by the end of the year, Y/N sees a way to make money. But will Peter's mental state change her outlook on the deal with Flash, or will she be too focused on winning the game? Disclaimer: I do not own Marvel or any of its characters. This story takes place after Endgame, but as if Far From Home didn't happen. This story mentions suicide, self-harm, and other triggering topics. Warnings will be provided before each chapter.