My Date with Drew

My Date with Drew

Directed by Brian Herzlinger, Brett Winn, Jon Gunn

Produced by rusty bear entertainment, lucky crow films

200590 min5.9 / 10

A charming, earnest documentary about an ordinary man's quixotic quest to ask his childhood crush on a date, blending humor, vulnerability, and genuine affection.

Ever since the second grade when he first saw her in E.T. The Extraterrestrial, Brian Herzlinger has had a crush on Drew Barrymore. Now, 20 years later he's decided to try to fulfill his lifelong dream by asking her for a date. There's one small problem: She's Drew Barrymore and he's, well, Brian Herzlinger, a broke 27-year-old aspiring filmmaker from New Jersey.

Questions people ask

  • Is My Date with Drew violent? No. Less violent than 92% of films.

  • Does My Date with Drew end with hope? Yes. More hopeful than 85% of films.

  • Is My Date with Drew scary? Barely. Less frightening than 84% of films.

  • Is My Date with Drew easy watching? Yes. More comforting than 82% of films.

  • Is My Date with Drew sad? Not especially. Less sad than 73% of films.

These describe how the film comes across, measured across the whole film and compared with other well-known films. They are not a content list — nothing here was counted or checked scene by scene, so for age-suitability or specific content use a classification board or a dedicated content-warning service.

28/ 100

Cinnamon Score

How much this film gives you that nothing else will, and whether it delivers.

You have seen this shape before.

Rarity29

How unlike any other film this one feels

Surprise37

How much more it delivers than it promises

Love20

How much audiences actually like it

The highest scores in the catalogue →

Ensemble

Like My Date with Drew

Nearest across the full emotional profile.

Same Mood as My Date with Drew

Nearest on what's most distinctive about this one.

Like My Date with Drew, But Darker

Similar, pushed toward heavier and more intense.

Like My Date with Drew, But Lighter

Similar, pushed toward warmer and easier.

Like My Date with Drew, But Less Popular

Same territory, far fewer people have seen it.

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