How To Tell You're A Douchebag Poster

How To Tell You're A Douchebag 2016

★ 3.410 votes80 min📅 2016-01-25

In *How To Tell You're A Douchebag (2016)*, director Tahir Jetter crafts a sharp, introspective rom-com that follows Ray Livingston, a struggling Brooklyn blogger whose biting online persona masks his own romantic stagnation.

Director: Tahir Jetter

Cast

Charles Brice
Charles Brice
Ray Livingston
DeWanda Wise
DeWanda Wise
Rochelle Marseilles
William Jackson Harper
William Jackson Harper
Jake Brown
Alexander C. Mulzac
Paul Kettering
Jenna Williams
Yasmin Ortiz
Tonye Patano
Tonye Patano
Miss Lady
Elise Rovinsky
Elise Rovinsky
Pam
Nicholas M. Garofolo
Nicholas M. Garofolo
Reza
Bianca LaVerne Jones
Bianca LaVerne Jones
Bianca
Ellie Foumbi
Ellie Foumbi

Frequently Asked Questions

What is *How To Tell You're A Douchebag* (2016) about?

*How To Tell You're A Douchebag* follows Ray Livingston, a self-proclaimed relationship blogger whose biting online persona hides his own romantic frustration. After a disastrous week spirals into a public confrontation with a stranger, Ray's carefully crafted cynicism is put to the test in this witty, New York-set comedy.

Who directed *How To Tell You're A Douchebag*?

The film was directed by Tahir Jetter, a filmmaker known for his sharp, character-driven storytelling and urban narratives.

Who stars in *How To Tell You're A Douchebag*?

The film stars Charles Brice as Ray Livingston, alongside DeWanda Wise, William Jackson Harper, Alexander C. Mulzac, and Jenna Williams in key roles.

Is *How To Tell You're A Douchebag* (2016) worth watching?

With its blend of sharp humor and relatable themes, *How To Tell You're A Douchebag* delivers a fresh take on rom-com tropes. While IMDb hasn't rated it, its 80-minute runtime and engaging cast make it a breezy, enjoyable watch for fans of character-driven comedies.

How long is *How To Tell You're A Douchebag*?

The film has a runtime of 80 minutes.

About How To Tell You're A Douchebag (2016) — A Sharp NYC Rom-Com with Heart and Humor

In *How To Tell You're A Douchebag (2016)*, director Tahir Jetter crafts a sharp, introspective rom-com that follows Ray Livingston, a struggling Brooklyn blogger whose biting online persona masks his own romantic stagnation. When a misguided rant lands him in hot water with Rochelle Marseille—a sharp-witted stranger he'd just berated—Ray's manufactured world of cynical dating advice unravels. Shot through with wit and urban grit, the film blends humor with poignant themes of self-reflection and growth.

As Ray navigates the fallout of his viral missteps, he's forced to confront the hollow reality behind his public brand. With a standout cast led by Charles Brice and DeWanda Wise, the 80-minute comedy balances satire with sincerity, making it a must-watch for fans of character-driven rom-coms and New York-centric storytelling.