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My Date with Drew

2004 · 90 min · Director: Jon Gunn, Brian Herzlinger, Brett Winn, Jon Gunn ★ IMDb 6.4 · 4,822 ratings

Show plot summary (may contain spoilers)

"If you don't take risks, you'll have a wasted soul." - Drew Barrymore. 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. But that doesn't stop Brian and his film school pals from doing everything they can think of to convince Barrymore to go out with him - and documenting their quest along the way. Equipped with a video camera they have to return to Circuit City in 30 days and the $1,100 Brian won on a game show (where the winning answer was, prophetically, "Drew Barrymore"), they've got one month to accomplish their mission. To succeed, they'll need to negotiate an army of publicists, agents, producers and assistants who surround the star so Brian can pop the question. My Date with Drew is the award-winning, inspirational story of an ordinary guy who, despite incredibly long odds, puts everything on the line to pursue his lifelong dream. It's also an astute and often hilarious look at contemporary dating rituals, the culture of celebrity and the power of passion.

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Emotional fingerprint

My Date with Drew (2004) — Movie. Top emotional signals: Humor 30%, Anticipation 25%, Inspiration 20%. Source: AI estimate. Shares describe emotional signal, not percentages of people. Your experience may differ. How we measure

  1. Humor30%
  2. Relief10%

AI estimate · no viewer votes yet

How we measure

AI estimate

Share of emotional signal, not the percentage of people or a probability of enjoyment.

Each viewer contributes one response, split equally across their selected emotions. When available, an automated estimate supplies a prior that is blended with those responses. Counts include distinct viewers, not automated estimates or archived anonymous votes. Fewer than 3 viewers is an early estimate; more responses do not guarantee certainty.

Why it feels this way

The strongest emotional signals are Humor, Anticipation, Inspiration. Genres: Documentary. AI estimate.

Is it worth watching?

Consider this title if you are looking for Humor, Anticipation and Inspiration. Its IMDb rating of 6.4/10 suggests a generally positive audience reception. For these leading emotions, its Feel Score is 66/100.

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Viewer responses about feelings after the title ended, separate from feelings while watching. No AI estimates.

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Cast

BD
Bill D'Elia

Self

LR
Lily Rains

Drew Look-alike

GD
George DelHoyo

Self - Voice Trailer Guy

AL
Andrea Logan White

Self - Trainer

Natasha Henstridge

Self (archive footage)

Cameron Diaz

Self (uncredited)

Griffin Dunne

Self (uncredited)

Samuel L. Jackson

Self (uncredited)

ML
Matt LeBlanc

Self (uncredited)

Lucy Liu

Self (uncredited)

Kevin Smith

Self (uncredited)

Bruce Willis

Self (archive footage) (uncredited)

Andy Dick

Self

Details

Directed by
Jon Gunn, Brian Herzlinger, Brett Winn, Jon Gunn
Type
Movies
Released
2004
Runtime
90 min
Country
United States
Ratings
★ IMDb 6.4 · 4,822 ratings
Feels mostly
Humor
Data updated

Where to watch

Data: JustWatch · Wikidata

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Emotion overlap shows mood similarity, not a prediction of enjoyment.