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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What did you think of 50 First Dates? Leave a comment below or share your favorite moment from the film!

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

Movie Review: 40 Days and 40 Nights (2002) – A Celibacy Challenge Rom-Com That Falls Short

Movie Review: 40 Days and 40 Nights (2002) – A Celibacy Challenge Rom-Com That Falls Short 

Tags 40 Days and 40 Nights review, Josh Hartnett, romantic comedy, Shannyn Sossamon, 2000s movies, Michael Lehmann, sex comedies, movie reviews, celibacy in movies, raunchy comedies 

  

 Overview

40 Days and 40 Nights is a 2002 romantic comedy directed by Michael Lehmann. It stars Josh Hartnett, Shannyn Sossamon, and Vinessa Shaw, and centers on a young man who takes a vow of celibacy for Lent — only to meet the perfect girl the moment he swears off sex.

Plot Summary

Matt (Josh Hartnett) is a San Francisco web designer heartbroken from a recent breakup. Tired of meaningless hookups, he decides to give up sex — and all forms of intimacy — for 40 days during Lent. Naturally, right as he embarks on this personal detox, he meets Erica (Shannyn Sossamon), a witty and charming woman who might be exactly what he’s been looking for. Complicating matters, Matt's roommate Ryan discovers the vow and turns it into a public spectacle by launching a betting site on whether Matt can last the full 40 days. As temptations escalate and misunderstandings pile up, Matt’s challenge quickly becomes more about emotional honesty than just abstinence.

What Works

• Performance: Josh Hartnett is affable and occasionally funny in the lead, and Shannyn Sossamon brings a low-key charm to a thinly written love interest.
• Direction: Michael Lehmann (known for Heathers) keeps the film briskly paced and visually polished, even if the story struggles to maintain momentum.
• Concept: The inversion of the usual “guy trying to get laid” trope is refreshing in theory, giving the film a unique starting point in the raunch-com genre.

What Doesn’t Work

• The plot relies heavily on contrivances and avoids real emotional stakes, opting instead for sitcom-level misunderstandings.
• Most supporting characters, especially Matt’s roommate, veer into caricature territory, and the film uses gross-out gags as filler rather than real humor.

Final Thoughts

40 Days and 40 Nights is a watchable but forgettable entry in the early 2000s rom-com scene. While it starts with a clever premise, the execution leans too heavily on clichés and easy laughs. Fans of Josh Hartnett or early-2000s nostalgia may find it mildly entertaining, but for most viewers, it’s a middling experience.

Rating

⭐ Rating: 2 out of 5 stars

What did you think of 40 Days and 40 Nights? Leave a comment below or share your favorite (or most cringeworthy) moment from the film!

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