Set against the vibrant backdrop of Brooklyn, How to Tell You’re a Douchebag follows Ray Livingston, a brash blogger whose public takedown of a rising Black feminist writer ignites a firestorm—both online and in his personal life. As Ray confronts the consequences of his arrogance, the film explores the complexities of love, accountability, and identity in the digital age.

Produced with wit and emotional clarity, this indie feature premiered at the Sundance Film Festival and became a standout for its fresh perspective on Black millennial relationships. With sharp writing and grounded performances, the film dissects what it means to grow up—and show up—in a world where your words carry weight.

Awards