Standup comedian and hopeless romantic Aaron Pelton faces a perplexing predicament when he is forced to relive the day his first girlfriend broke up with him, over and over again. As he endures repeating the same cycle of steak dinners, sombre pond-side strolls, and bro vent sessions, Aaron grapples with understanding why this is happening to him and what personal growth could possibly come from constantly re-experiencing the worst day of his life. Through this journey of heartbreak and self-reflection, Aaron discovers more about himself, his flaws, and his capacity to evolve.