10 Movies That Both You & He Will Enjoy
The Princess Bride (1987). Source: Winnipeg Film Group
Let’s face it: dating can be terribly stressful — guessing what someone else is thinking, reading signals, figuring out what they like (or don’t like). But a wonderful way to take the pressure off for a night is to watch a movie together.
But wait — which movie? It’s crucial to find a film that will entertain, interest, and appeal to the both of you, while also giving you enough to talk, laugh, or think about together afterwards.
Easier said than done, right? Well, not necessarily — we’ve compiled a few of the best date night movies that are sure to have something intriguing for the both of you!
Hello, World!
The Princess Bride (1987)
For a lighter watch that will leave you both laughing and on the edge of your seat. Pop in this cult classic, full of puns, sword fights, adventure, romance, and fantasy about a masked man winning the heart of his one true love while surviving a never ending barrage of fantastical obstacles. The Princess Bride has just enough adventure and romance for literally anyone to love. Starring Robin Wright, Billy Crystal, Fred Savage.
Knives Out (2019)
If you’re looking for a fun, intriguing, suspenseful mystery movie, look no further than Knives Out. This Agatha Christie-esque murder mystery will both excite the mind and tickle the funny bone as together with your date you can try and figure out who-dunnit before the final reveal! Starring Daniel Craig, Ana de Armas, Chris Evans, Jamie Lee Curtis, Toni Collette.
The Map of Tiny Perfect Things (2021)
This 2021 release focuses on a teenaged boy and girl find themselves trapped in the same day, repeating and living through it over and over again — and it’s sure to entertain, touch, and spark deep, intriguing thoughts. Asking some big philosophical questions about life while kindling a romance, The Map of Tiny Perfect Things will be one that can connect to both you and your date. Starring Kathryn Newton, Kyle Allen.
500 Days of Summer (2009)
Tom is a shy, sweet, hopeless romantic that works as a writer at a greeting card company. When Summer starts working with him, he’s absolutely sure she’s the girl for him. But despite being interested in him as well, Summer has her reservations. 500 Days of Summer beautifully and deeply explores the inner workings of modern dating, what love truly looks like, the pain of heartbreak, and the importance of personal growth. Starring Joseph Gordon-Levitt, Zooey Deschanel.
A Quiet Place (2018)
In a world that’s been taken over by horrifying monsters that rely on their heightened sense of hearing to hunt their prey, we watch as a husband and wife work to protect their family from the evil creatures that threaten them at almost every turn — creating an odd mixture of getting our adrenaline pumping while warming our heart. Be touched and terrified as you watch, entertaining you both and leaving you asking each other the question “what would you do?”. Starring John Krasinski, Emily Blunt.
Crazy, Stupid, Love. (2011)
This star-studded movie quickly became a favorite after it premiered in 2011. With both serious, weighty themes like divorce and depression perfectly mixed with hilarious dialogue and situations this will be a crowd-pleaser for the both of you. A story about falling out of and into love and the struggles of growing up, Crazy, Stupid, Love will connect with any audience. Starring Emma Stone, Ryan Gosling, Steve Carell, Julianne Moore.
Charade (1963)
This exciting, intriguing mystery is sure to have you both captivated the whole time. After Regina’s husband is murdered, she enlists the help of Peter, a handsome man she met while on a skiing vacation in the French Alps. We follow along as the two chase down their three shifty suspects. Soon, Regina begins to wonder who she can trust, if anyone at all. Starring Audrey Hepburn, Cary Grant.
A Knight’s Tale (2001)
This beautiful, medieval-set film centers on William, a peasant who’s determined to change his life for the better by winning over a lovely maiden. Filled with wonderful side characters, romance, charmingly comedic moments, and jousts, A Knight’s Tale is a movie that has a little something for everyone. Starring Heath Ledger, Shannyn Sossamon, Paul Bettany.
Eternal Sunshine of the Spotless Mind (2004)
In this incredibly artistic, aesthetically beautiful, and heartbreaking movie, we follow the dynamic, introverted Joel, a heartbroken man who’s chosen to have his memory erased to escape the pain of his last relationship before falling in love with the enigmatic and troubled Clementine. Filled with romance, heartbreak, sci-fi themes, and some of the best acting and writing around, this film will most certainly offer you hours of conversation after the credits. Starring Kate Winslet, Jim Carrey.
La La Land (2016)
In this colorful, whimsical movie-musical, Mia, an aspiring actress living in LA, meets and quickly falls for Sebastian, a jazz pianist who dreams of opening his own jazz club. We watch as their relationship blooms, as challenges bud, and as they come closer and closer to their ultimate dreams. La La Land wrestles with the question of what true fulfillment looks like, all while mixing in beautiful dance sequences and wonderfully catchy musical numbers. Starring Emma Stone, Ryan Gosling.