When her life is disrupted with a call from an old boyfriend, Jill takes a second to scrutinize her unfulfilling dating life, reexamine their relationship and ponders the possibility of a second chance. But is he really the one who got away, or did she dodge a bullet? Jill decides this question is definitely worth further consideration. Across the country, Jim and his friend frequently trade dating woes and this has lead Jim to his own existential crisis. In the process, he is caught in a struggle between who he is and trying to figure out who he wants to be, often defaulting to his current self while trying to chart a path forward.