In a charming and chaotic corner of Chicago, Rob Gordon, a passionate record store owner, finds himself caught in an emotional whirlwind after a breakup with his girlfriend, Laura. As he tries to understand why his relationships always end in disaster, Rob decides to take an inventory of his lost loves, chatting with his ex-girlfriends to uncover the truth behind his romantic missteps.
Through his quirky interactions, Rob explores his failures and successes, while his circle of friends, including the sarcastic buddy Dick and the restless Barry, provide their own perspectives on love and music. Each conversation becomes a journey of self-discovery, where the soundtrack of his life blends with moments of nostalgia, laughter, and heartbreak. As he sifts through his playlists and discovers what love truly means, he also faces the possibility of reconnecting with Laura.
In a sea of records, playlists, and deep connections, Rob realizes that the real challenge is not just finding his next relationship, but understanding himself and what he truly seeks in life. The film is a fresh and funny reflection on identity, music, and the ups and downs of romantic relationships, capturing the essence of what it means to love and lose in the process.