The 10 Best Romantic Movies To Watch With Your Boyfriend

Is there anything sweeter than kicking back and cuddling up with your man while watching a beautiful, tear-jerking romantic movie? I know, I know, you love it, but your boyfriend likely isn’t that keen on romantic flicks. Don’t worry, though, because I got you covered.

From a guy’s perspective, I’m bringing you the ultimate list of the ten best romantic movies to watch with your boyfriend that even he’ll definitely enjoy. I’m not talking about the classic rom-com cookie cutters (though there is one or two on the list) – but real, awesome, deep romantic films that will pique your interest as much as his. Enjoy!

Honorable mentions

If you’re here to find that perfect romantic comedy, this is about as far as you’ll get in this article. Still, I’ve picked two that I kind of enjoyed that you could play on a boring, rainy day with your guy and actually have fun.

The first one is ‘He’s Just Not That Into You’ (2009) – a movie with an all-star cast, a ton of great humor, adultery, and a couple of really nice life lessons along the way. The movie connects numerous separate storylines and interconnects them in a fun way, showing how our interpretation of human behavior can often be totally different from what it actually is.

If you’re on Netflix and you’re looking for something a bit more modern, then you won’t make a mistake with ‘To All the Boys I’ve Loved Before’ (2018). It’s about a teenager who writes love letters to her previous love interests, but she never sends them out. However, her own sister leaks them and exposes her, causing all kinds of problems for her social and love life.

It’s funny, sweet, and actually quite well-written, so I do recommend giving it a go if you’re in the rom-com mood. Now, on to the more serious, and deeper films on the list.

10. ‘One Day’ (2011)

IMDb score: 7.0/10

What it’s about: Dexter and Emma hooked up on the night of their college graduation, but the relationship never went any further despite their attraction. The movie follows both of them for one day a year over the next twenty years – that very same date they spent the night together. Sometimes we see them together, sometimes not, until the very final day when fate does her bidding.

Why you should watch it: This is quite a unique, beautiful movie, but it has real depth and value, showing how life works in mysterious ways, but also how fleeting and uncertain every moment is, which is why you should never wait for that next good moment – seize it right now and make every moment great. You never know when that can become impossible…

9. ‘Midnight in Paris’ (2011)

IMDb score: 7.6/10

What it’s about: Gil is a screenwriter who takes a trip to Paris with his fiancee and her family. One evening, he takes a midnight stroll that mysteriously takes him back to the 1920s, where the cream of European society from the decade shares his table with him, like Scott Fitzgerald, Ernest Hemingway, and others.

Why you should watch it: This is one of the most beautifully directed movies of all time, and for me, Woody Allen’s crown jewel of his career as a director. It’s funny at moments, but the story is brilliant and esthetically breathtaking, and there’s just enough romance in there to fit the list, but not too much to be overwhelming. I couldn’t recommend ‘Midnight in Paris’ more.

8. ‘About Time’ (2013)

IMDb score: 7.8/10

What it’s about: When he was 21, Tim realized he had the ability to time travel and change everything that happened in his life – so he decided to go back and get himself a girlfriend. However, changing the past isn’t that simple, and naturally, Tim’s actions have consequences.

Why you should watch it: ‘About Time’ dabs into science fiction a bit, and has a ton of comedic elements to it, but it is far from a comedy if you ask me. The ending will leave you sobbing, trust me, but it’s simply a beautiful film that’ll leave no one emotionless.

7. ‘The Curious Case of Benjamin Button’ (2008)

IMDb score: 7./10

What it’s about: Benjamin Button’s story is quite a unique one. Through mysterious circumstances, Benjamin Button is born an elderly man and starts aging backward throughout his life. 

Why you should watch it: Many people don’t consider ‘The Curious Case of Benjamin Button’ to be a romantic movie, but it most certainly is. It’s one of my favorite movies that taps into the concept of time and life in a very unique way. Cate Blanchett is incredible, but Brad Pitt delivers this performance with a unique verve. I cried like a baby in the end. Pun intended.

6. ‘The Notebook’ (2004)

IMDb score: 7.8/10

What it’s about: Duke is an elderly gentleman in a retirement home, where he devotedly reads a captivating love story to his fellow tenant Allie, who has dementia, every day from his old notebook. It’s a story of a young couple whose social status almost separated them, but they never gave up on their love. How does this story end? Does it ever end, or does it start right back tomorrow?

Why you should watch it: I’m not that big on romantic movies, especially not tear-jerkers, but I can always rewatch ‘The Notebook.’ The movie is based on a book by Nicholas Sparks, it’s a story of everlasting, undying love that penetrates all boundaries, but at the same time, it’s so heartbreaking that you’ll wonder why you chose to watch it in the first place.

5. ‘Roman Holiday’ (1953)

IMDb score: 8.0/10

What it’s about: HRH Princess Ann is on a tour of Europe, now visiting Rome – but Ann hates her life as a political figure, with a strict regimen, always having to do and say what she is told with no freedom whatsoever. Once in Rome, she meets an American reporter, and disguises herself to spend the holiday with him and finally live a little…

Why you should watch it: There’s a reason why ‘Roman Holiday’ is dubbed as an all-time classic. Audrey Hepburn and Gregory Peck in the main roles with William Wyler as the director and the legendary Dalton Trumbo as one of the writers – it’s a recipe for a fantastic movie that beats the teeth of time.  If you’re a fan of old-timey flicks, this is one of the best ever.

4. ‘Her’ (2013)

IMDb score: 8.0/10

What it’s about: The story takes us into the near future where a lonely writer named Theodore has AI software – or rather, an operating system that is designed to meet his every need. However, Theodore forms a unique bond and somewhat of a relationship with the system.

Why you should watch it: When my girlfriend suggested this film to me, the premise sounded super weird to me. It felt too close to home, with AI advancing so much over the past years. It turned out to be a spectacular film with an all-star cast of Joaquin Phoenix, Amy Adams, Chris Pratt, and the voice of Scarlett Johansson, and a really deep, phenomenal film that’ll leave you questioning everything.

3. ‘La La Land’ (2016)

IMDb score: 8.0/10

What it’s about: A talented but struggling jazz pianist falls in love with an actress in Los Angeles. They dream of a future together, but their versions of what it should look like dramatically differ. Will their love prevail, or will their differences cause them to grow apart?

Why you should watch it: As the movie’s tagline says – ‘Here’s to the fools who dream.’ This movie will stand the test of time because it’s really just utterly incredibly well-crafted. The story is awesome, and believe me, even if your man doesn’t like musicals – if he has any affinity for jazz and for art, he will absolutely love ‘La La Land.’  It’s a smart movie with a super surprising ending. I won’t spoil it, but Emma Stone and Ryan Gosling played the roles of a lifetime here.

2. ‘Before Sunrise’ (1995)

IMDb score: 8.1/10

What it’s about: A man and a woman travel separately in Europe and meet on a train. They end up spending one day, and one evening together in Vienna, but despite their incredibly powerful connection, they realize they likely won’t see each other again, so they make the most out of their time together by getting to know each other on the deepest level.

Why you should watch it: This entire trilogy – ‘Before Sunrise,’ ‘Before Sunset,’ and ‘Before Midnight’ – is by far my favorite in the romance genre. It’s not a classic romantic flick where you get to see love, betrayal, or even a years-long relationship. Nay – you get to see a single day in the life and romance of a couple who just met on a train in Europe. The entire movie is a dialogue between them that is incredibly deep and somewhat philosophical, but it’s so well written and executed that you’ll feel as if you were watching an action flick. I highly recommend this film, as well as the two sequels.

1. ‘Eternal Sunshine of the Spotless Mind’ (2004)

IMDb score: 8.3/10

What it’s about: When a couple breaks up on bad terms, the man finds out his ex underwent a medical procedure to have him completely wiped out of her memory. Angrily, he decides to return the favor by doing the same. However, as the procedure starts, he realizes that the memories they shared are too valuable, so he tries everything he can not to lose the memory of her…

Why you should watch it: Last but not least, you’ll probably see this film a lot on my lists if the topic at hand fits the movie, because to me, ‘Eternal Sunshine of the Spotless Mind’ is a masterpiece. For half of the movie, I scream, ‘No! Run. RUN!’ and it breaks my heart every single time. It teaches you that you have to take the bad with the good. The bad times make the good times ten times better. Every precious memory you have with your better half is a unique testament to the love that once was, even if it isn’t there anymore. The film takes a little thinking, but once the end credits roll, you and your man will hold each other closer than you ever had before.

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