After getting dumped by his childhood sweetheart, Charlie Park finds himself at rock bottom. Despite all efforts by his best friend; RJ, a female firecracker who may or may not be contributing to his woes, Charlie cannot break free from this rut. His new status quo is filled with incessant cleaning, obsessing over his favorite daytime talk show host, and crafting the definitive list that will help him discover the perfect woman. That’s when Charlie’s apartment burns to the ground, proving that life can always get worse. But thanks to a chance encounter with a waitress, Charlie musters the courage to move from Los Angeles to Chicago in search of a fresh start. Given a clean slate, Charlie trades in his 401K for a minimum wage job, finds a group of friends who teach him the significance of being a Chicagoan, and bunks up with an unexpected roommate. Along the way, he fumbles through a new series of romances… and a few old ones, too! Regardless of these missteps, if Charlie plays his cards right, he just might end up with everything he’s always wanted. Or so he thinks.