Movie Review: 50 First Dates (2004) – A Surprisingly Sweet Sandler Romance with a Twist

Movie Review: 50 First Dates (2004) – A Surprisingly Sweet Sandler Romance with a Twist 

Tags 50 First Dates review, Adam Sandler movies, Drew Barrymore, romantic comedies, memory loss romance, Hawaii films, 2000s rom-coms, Peter Segal, best rom-coms, comedy movie reviews, GuessTheGross, Valentine’s Day movies 

 Overview

50 First Dates is a 2004 romantic comedy directed by Peter Segal. It stars Adam Sandler and Drew Barrymore in a love story set in Hawaii, where a woman’s rare memory condition forces her suitor to win her heart anew each day.

Plot Summary

Henry Roth (Adam Sandler) is a carefree veterinarian living in Hawaii who enjoys casual flings with tourists—until he meets Lucy Whitmore (Drew Barrymore), a charming local woman with a unique condition. After a car accident, Lucy suffers from short-term memory loss and relives the same day every morning. Despite the challenge, Henry falls for her and commits to making her fall in love with him again and again. Along the way, he navigates her protective family, oddball friends, and his own immaturity in a quest for lasting love.

What Works

• Performance: Drew Barrymore brings sweetness and emotional complexity to Lucy, grounding the outlandish premise. Sandler tones down his usual goofiness to deliver a surprisingly likable romantic lead.
• Direction: Peter Segal smartly balances romance and comedy, keeping the tone light while letting the emotional beats shine through.
• Tension or Themes: The film explores themes of memory, commitment, and daily devotion with a surprisingly sincere touch, especially for a Sandler vehicle.

What Doesn’t Work

• The subplots—particularly those involving Sean Astin and Rob Schneider—veer into juvenile territory and feel disconnected from the emotional heart of the story.
• Some humor falls flat, relying on stereotypes and bodily gags that clash with the film’s more heartfelt core.

Final Thoughts

50 First Dates is one of Adam Sandler’s most balanced romantic comedies, blending his trademark silliness with genuine sweetness. While not without its flaws, the chemistry between Sandler and Barrymore elevates the film, making it a memorable Valentine’s Day treat or anytime date-night watch.

Rating

⭐ Rating: 3.5 out of 5 stars

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If you enjoyed this review, check out my takes on other romantic comedies here.

Movie Review: 50 First Dates

50 First Dates (2004) 

Directed by Peter Segal 

Written by George Wing 

Starring Adam Sandler, Drew Barrymore, Blake Clark, Sean Astin, Dan Akroyd, Rob Schneider

Release Date February 13th, 2004

Published February 14th, 2004  

Adam Sandler has charted a strange career trajectory to becoming the highest paid actor in Hollywood. His films have run the gamut from awful to extraordinarily awful.  Then came Punch Drunk Love, Sandler's teaming with indie genius P. T Anderson, an unbelievable transformation into a real actor. Unfortunately, it didn't last. Sandler quickly regressed with the dreadful cartoon 8 Crazy Nights and a pair of mediocre live action comedies, Mr. Deeds and Anger Management. His latest film, 50 First Dates, continues Sandler's weird career twists and turns. A film that combines Sandler's best work since Punch Drunk Love and more of his most juvenile humor.

In 50 First Dates, Sandler is Henry Roth, a ladies man of mythic proportion. His legend is spread by the innumerable woman he meets while living in the vacation capital of Hawaii. Bedding vacationers and sending them off with some story of secret identities, or any other number of lies, Henry does all he can to avoid romantic entanglements. That is, until Henry meets Lucy Whitmore (Drew Barrymore), a flighty blonde teacher who eats at the same café every morning, reading the same Sunday newspaper, wearing the same outfit.

Odd? Indeed, and the explanation is even weirder. It seems Lucy was in an accident a year ago and as a result suffered a head injury that destroyed her short-term memory. Every night when she goes to bed her mind resets to the day of the accident. Her father Marlin (Blake Clark) and brother Doug (Sean Astin), not knowing how to deal with the situation, choose to relive the same day with her until they can find some other way to deal with it.

Despite the complicated nature of Lucy's condition, Henry can't resist her charm and begins finding different ways to introduce himself to her everyday. Eventually he even wins over her family and the romance grows as Henry sets about making Lucy remember him somehow and making her fall in love again everyday.

It's a concept that requires some suspension of disbelief but with Drew Barrymore's performance, that suspension is not hard at all. Barrymore delivers her best performance since she made Sandler somewhat less painful to watch in The Wedding Singer. It is her surprisingly complex, sweet performance that sells the far fetched memory loss concept and helps Sandler raise his game to the point where he actually assuages his usually cocky, doofus persona for a more laid back romantic sweetness that really works for him.

This is still an Adam Sandler film however, and his trademark juvenility is still in place. The difference in this film is that instead of Sandler wallowing in the film’s low humor, director Peter Seagal and writer George Wing smartly lay the film’s worst jokes on the supporting cast. That includes Sean Astin, lowering himself from the Oscar caliber Lord of The Rings to a subpar subplot as Barrymore's steroid abusing brother and Lusia Strus, an asexual security guard. Sandler's usual backup guys like Rob Schneider and Allen Covert are also along for the ride.

These subplots don't work but written with some distance from the main romantic plot, they do allow Sandler some separation from his usual antics allowing him to focus on being a likable, believable romantic lead. He pulls it off with romantic flourish, and an acceptable amount of sappy sentimental romance.

This Valentine's treat is one of the better romantic comedies of the last few years. In a genre that has suffered from formulaic plots and tired clichés it's not hard for a film like 50 First Dates to stand out. Still, I must give Sandler credit, when he wants to he can surprise you.