The best (and worst) movies to watch with your Valentine

Editor’s Note: This article is a review and includes subjective thoughts, opinions and critiques. 

This review contains spoilers.

Best: “A Charlie Brown Valentine” (2002) by Bill Melendez — Melita D’Souza ’29

If you’re looking for a sweet, nostalgic and heartfelt Valentine’s Day flick, “A Charlie Brown Valentine” might be the best choice. Unlike flashy rom-coms, this Peanuts special focuses on the awkward, hopeful and sometimes disappointing side of love. Charlie Brown’s longing for a Valentine feels relatable and sincere, reminding us that love isn’t always perfect, and that vulnerability is part of the experience. Charlie Brown makes you laugh at those awkward childhood memories and reminds you what it felt like to have a simple, innocent crush.

Best: “The Love Witch” (2016) by Anna Biller and Worst: “Together” (2025) by Michael Shanks — Melisa Guleryuz ’27

Whether you’re single or taken, “Love Witch” is the perfect movie to watch on Valentine’s Day, because it’s two hours of heart-shaped cocktails, tarot readings about true love, satin gowns and a witch who believes romance should be worship-level intense (and actually does something about it!). On the other hand, the new romance-horror “Together” is a diabolical pick because instead of roses and butterflies, you get relationship realism mocking codependence where a couple physically merges together over time — I’d want to schedule a couples therapy session mid-credits. 

Best: “10 Things I Hate About You” (1999) by Gil Junger — Miro Ohannes Swisher ’25 M.S. ’26

The best thing about “10 Things I Hate About You” is that it contains two love stories in one movie. This is ideal for a Valentine’s Day date early in a relationship, as you can interrogate your date afterwards about which couple is superior. If their answer isn’t Patrick and Kat, you can ask questions about how they came to the wrong answer and get a better understanding of where they might go wrong in your relationship down the line. Perhaps they are “without.” If their answer is Patrick and Kat, you can rest easy knowing that your partner is in fact correct and can be trusted when discussing major life decisions in the future together.

Best and Worst: “Gone Girl” (2014) by David Fincher — Blyss Cleveland, Ph.D. candidate

A psychological thriller and adaptation of Gillian Flynn’s eponymous best-selling novel, “Gone Girl” chronicles Amy Dunne’s disappearance on her and her husband Nick’s anniversary. As Nick becomes the prime suspect, flashbacks reveal the unraveling of their relationship. Though The Daily gave the film a mixed review, “Gone Girl” is infinitely re-watchable because of Rosamund Pike’s excellent portrayal of Amy. If you’re commemorating Valentine’s Day without a paramour, “Gone Girl” is a reminder to not let the fantasy of a relationship obscure the potential worst-case scenario: being partnered with someone who charms you, but grows to hate and plot against you! The film gives couples a litmus test of progressive values. Anyone can support women’s rights, but can the object of your affection support a wronged woman’s right to do wrong? Learn the answer to this question early to avoid living out Amy and Nick’s twisted love story!

Best and Worst: “How to Lose a Guy in 10 Days” (2003) by Donald Petrie — Caroline Cho ’29 

Ironically, “How to Lose a Guy in 10 Days” might be the best Valentine’s movie because it’s built on everything we’re told to avoid in relationships. While many rom-coms sell perfect soulmates, this film embraces messy relationships, ulterior motives and falling in love against your will. Andie and Ben’s mutual deception — her sabotaging for an article, him dating her for a bet — is flawed but refreshingly honest about the personas we perform in early dating. Love doesn’t require perfection. Watching our protagonists juggle competing agendas while accidentally catching real feelings feels more genuine than sanitized romance. On the flip side, it’s the worst pick if you believe Valentine’s should celebrate trust and authenticity, because this couple literally built their foundation on professional manipulation. Your mileage may vary depending on whether you find “we lied our way into love” cynically romantic or just deeply concerning.

Worst (Best?): “Thank You for Smoking” (2005) by Jason Reitman — Daniel Xu ’29

Adapted from Christopher Buckley’s 1994 novel of the same name, Reitman’s directorial debut — featuring Nick Naylor as a literal spokesperson for Big Tobacco — contains a number of sins and gems. “Thank You for Smoking” is decidedly unromantic: one can’t help but feel slimed out as Naylor bribes anti-tobacco advocates and blatantly lies about the carcinogenic properties of cigarettes. Still, it’s undeniable that “Thanks for Smoking” is peak American consumerism. Valentine’s Day has always had a consumerist bent, and one could very well imagine how Naylor would project the tobacco industry’s failings onto this uniquely unhealthy yet charming holiday. 

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