The 10 Best Date Night Movies That You And Your Partner Will Actually Love

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The Great Gatsby

I believe The Great Gatsby (2013) is one of the most underrated romance movies of all time. Based on the iconic F. Scott Fitzgerald novel, this energetic film adaptation captures the longing between Jay Gatsby and Daisy Buchanan more effectively than the original book! It’s the ultimate tale of pining for what might have been, and doing everything within your power to win over the love of your life, even if that means throwing grand, elaborate parties just out of the hopes that she’ll happen to stumble in one day! In my opinion, no one who has portrayed Gatsby in earlier adaptations can compare to Leonardo DiCaprio.

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Moonrise Kingdom

Moonrise Kingdom (2012) is one of those charming date-night movies that everyone feels good about. Directed by Wes Anderson, this whimsical coming-of-age love story follows two 12-year-olds, Sam and Suzy, who run away together after forming a deep, instant connection that no one around them seems to understand. It’s innocent, quirky, and quietly emotional in a way that sneaks up on you.

What makes it such a great date-night watch is its balance of sweetness and humor — it’s romantic without being cheesy, heartfelt without trying too hard. The dreamy New England setting, nostalgic soundtrack, and perfectly symmetrical visuals make it feel cozy and transportive, like escaping into a storybook for a couple of hours. And honestly, there’s something incredibly refreshing about a love story that reminds you what it felt like to fall for someone for the very first time — awkward and full of hope.

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When Harry Met Sally

You want slow burn? Harry and Sally practically invented the genre! If you’re a sucker for the friends-to-lovers trope, and you love a good fall foliage backdrop in NYC, you basically have no choice but to stream this unforgettable rom-com. It’s practically medicine for the hopeless romantics.

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Sleeping With Other People

Here’s a bit of a modern twist on the When Harry Met Sally set up. When two love addicts decide it’s best to avoid dating each other due to their tendency to cause romantic destruction, they end up realizing they’re practically destined to be together. Yikes!

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10 Things I Hate About You

10 Things I Hate About You (1999) is one of the greatest romantic comedies of all time, and no one can convince me otherwise. Loosely inspired by Shakespeare’s The Taming of the Shrew, this late-’90s classic perfectly captures the chaos, vulnerability, and thrill of falling for someone when you least expect it.

What makes it such a perfect date-night movie is its mix of humor and heart. You get sharp banter, unforgettable one-liners, and that iconic Heath Ledger serenade scene (which alone deserves a rewatch). Beneath all the teen-movie fun, though, there’s a surprisingly emotional love story about learning to let your guard down and being brave enough to care. It’s funny, nostalgic, and endlessly rewatchable — the kind of movie that makes you swoon and quote it together long after the credits roll.

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500 Days of Summer

I think 500 Days of Summer (2009) is one of those date-night movies that hits differently depending on where you are in your love life. On the surface, it’s a quirky indie romance about boy-meets-girl, set to an incredible soundtrack and filled with charming, offbeat moments. But underneath it all, it’s really a story about expectations, and how easily we can fall in love with the idea of someone rather than who they actually are.

What makes it such a great date-night watch is that it sparks conversation long after the movie ends. You find yourself debating who was “right," and maybe even seeing your own love story a little more clearly. It’s funny, bittersweet, and emotionally honest — the kind of movie that makes you laugh together and feel a little nostalgic.

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The Proposal

Sandra Bullock and Ryan Reynolds’ chemistry in this film needs to be studied, seriously. It’s the ultimate enemies-to-lovers movie, with stellar performances from both actors. It’s also incredibly funny, mostly due to the brilliant Betty White.

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Crazy, Stupid Love

I think Crazy, Stupid, Love (2011) is one of those rare rom-coms that truly has something for everyone, which automatically makes it a perfect date-night pick. At first glance, it feels light and funny — complete with glow-ups, flirty banter, and laugh-out-loud moments — but underneath, it’s actually a surprisingly heartfelt look at love in all its messy stages.

What I love most is how the movie weaves together multiple love stories, from first crushes to long-term relationships trying to find their spark again. It’s one of those films where you’re equally invested in the laughs and the twists — and how can you both not love Ryan and Emma on screen together.

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Eternal Sunshine of the Spotless Mind

I think Eternal Sunshine of the Spotless Mind (2004) is one of the most hauntingly beautiful love stories ever put on screen. Starring Jim Carrey as the quietly heartbroken Joel Barish and Kate Winslet as the impulsive, unforgettable Clementine Kruczynski, the film explores what happens when love ends, and whether forgetting it would actually make things easier.

What makes this movie such a powerful date-night watch is how relatable it feels for anyone who has been heartbroken. As Joel relives memories of his relationship while they’re being erased, you watch the tenderness, frustration, joy, and heartbreak unfold in reverse. Carrey’s subdued performance is surprisingly vulnerable, while Winslet brings chaos, warmth, and emotional honesty to Clementine in a way that feels painfully real.

It’s not a traditional rom-com by any means, but that’s exactly why it works. The film asks big questions — about memory, regret, and whether loving someone is still worth it even if it ends in pain.

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Breakfast At Tiffany’s

Is there anyone more charismatic than Audrey Hepburn in this film? Her portrayal of the zany yet tragic New York socialite, Holly Golightly, is simply legendary. And that final kiss in the rain scene? We’re still swooning over it, all these decades later.