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A desperate man dates 20 women on camera and accidentally falls in love—ethics not included.
TMDB
53
IMDb
56
Rotten Tomatoes
35

20 Dates (1998)

cringe-core90s indie chaosmeta-romance

Overview

ComedyRomance

Myles is divorced in L.A. He wants a love life and a film career. So he decides to go on 20 dates and find true love in front of a camera, making his first feature. His patient agent, Richard, finds a $60,000 investor, the shadowy Elie. Myles starts his search, sometimes telling his date she's being filmed, sometimes not. Elie wants sex and titillation, Myles wants it "real." Myles regularly talks with his old film teacher, Robert McKee, who wonders if love is possible in modern life. Half-way through the 20 dates, Myles meets Elisabeth; she's everything he desires and she likes him. Can he finish the 20 dates, satisfy Elie, and complete his film without losing Elisabeth?

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Content warning
biographymockumentaryfound footagehidden camera
authenticity vs. performanceexploitation in artdesperation masquerading as ambition

Standout Aspects

Writing

Blurred reality where you can't tell documentary from scripted—intentionally or not.

Acting

Myles playing himself so hard you genuinely can't tell if it's brilliance or disaster.

Production

Made for $60K with the actual investor as a shadowy voice—commitment to bit.

Best for:Solo: Late-night viewing when you want to feel better about your own dating life.·Friends: Group watch to collectively scream at his questionable choices.·Rewatch: Second viewing to spot which dates are real and which are staged.
Heads up:Triggers: Filming women without full consent presented as quirky, not predatory.·Sexual Content: Elie's demands for 'titillation' create genuine uncomfortable power dynamics.
M

Director

Myles Berkowitz

ReleasedJan 1, 1998
Runtime1h 27m
StatusReleased

Vibe

Pacesteady
Intensitymedium
Tonemixed
Feelmedium
20th Century Fox
Fox Searchlight Pictures

Top Cast

Tia Carrere

Tia Carrere

Herself

Elie Samaha

Elie Samaha

Voice of the Producer (voice)

Julie McCullough

Julie McCullough

Self

Ask about 20 Dates

Opens AI chat

Deep Dive

Trivia, insights & behind the scenes

Trivia

Robert McKee appears as himself, making this possibly the only film where a screenwriting guru watches someone violate every ethical principle he teaches.

Cultural

Made during the '90s indie boom when 'mockumentary' meant 'we can't afford lights' and reality TV ethics didn't exist yet.

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