14 Timeless Romantic Comedies To Binge On Valentine’s Day

Published on January 29, 2021

February is the perfect time to binge on some classic romantic comedies. Even if you’re not the type to celebrate Valentine’s Day, everyone loves cuddling up with a nice glass of wine and watching people fall in love with some funny twists thrown in. Here are 14 timeless romantic comedies, in no particular order, to binge on Valentine’s Day.

1. Crazy Rich Asians – HBO Max

It might be strange to start a list of timeless romantic comedies with a movie that just came out in 2018, but Crazy Rich Asians was an instant classic. An American math teacher starts dating a man. She flies to Singapore to go to a wedding with him, and finds out his family is rich. Like, really rich. The characters are authentic and funny, and the love story rings true. For an added bonus, the fashion, jewelry, and sets are all absolutely phenomenal. This movie checks all the boxes, visually and emotionally, and you just can’t go wrong with this delightful film.

2. Mystic Pizza – Netflix

This is a lesser-known Julia Roberts film, but in my opinion, it’s some of her best work. Three women living in an east coast fishing town navigate young love, with varying degrees of success. As much as this movie is a romantic comedy, it has deeper layers about friendship and sisterhood that make it worth watching, even if you’re not feeling over-the-top romance this year. Mystic Pizza is down to earth, heartwarming, fun, and emotional. Watch Julia Roberts pour a bucket of fish into her boyfriend’s sports car. It’ll be great, I promise.

3. How to Lose a Guy in 10 Days – Amazon

Kate Hudson and Matthew McConaughey are a duo who will go down in romantic comedy history. The chemistry between these two is just *chef’s kiss*. A women’s magazine writer picks out a guy to test out her theory on everything women do wrong in relationships. An ad executive makes a bet that he can get any woman to fall in love with him. Shenanigans ensue. The plot of this film has lighthearted and silly moments without being overly raunchy, which I think is a sweet spot for romantic comedies. How To Lose a Guy in 10 Days goes perfectly with a box of Valentine’s Day chocolate.

4. Palm Springs – Hulu

This movie is unexpected and delightfully different than the other Rom-Coms on this list. It’s also totally not what you would expect from producer and star Andy Samberg. Two people go to a wedding in Palm Springs and get stuck in a time loop. They live the same day, at the same wedding over and over again. It’s truly enjoyable in a way that’s not just mindless entertainment. Also, beautiful Palm Springs landscape shots don’t hurt.

5. Pretty Woman – Amazon

Not watching this movie this Valentine’s Day would be a big mistake. Huge! This is one of those movies that’s just so iconic and recognizable, and for a reason. This is another Julia Roberts pick, but what can I say, the woman is the queen of romantic comedies. In this film, she plays a prostitute, who meets Richard Gere’s character out on the street. He needs someone to be his girlfriend, and after a legendary shopping trip, she’ll do perfectly. It’s a rags-to-riches love story that’s an undeniable classic.

6. The Princess Bride – Disney+

This, in my humble opinion, is one of the best movies of all time. Buttercup falls in love with a farm boy. He disappears, and she is forced to move on with her life. Later, Buttercup is kidnapped the night before her wedding to Prince Humperdink and a mysterious stranger shows up with impressive skills. It’s clever and sarcastic and yet still appropriate for most kids. It’s romantic and fun and also full of adventure. This movie will stand the test of time. Some of the special effects are now quite dated, but it doesn’t matter. The story and dialogue more than make up for a little 1980s’ style cinematic artistry.

7. Sixteen Candles – Amazon

There had to be at least one John Hughes movie on this list, and while Sixteen Candles has its problematic moments, it’s also the most romantic of Hughes’ works. Molly Ringwald stars as Samantha, a high school girl whose entire family seems to have forgotten about her birthday. She’s got a crush on the dreamy Jake Ryan, a senior. While we watch with a different lens in 2021, it’s still a classic, and the love story between Samantha and Jake is a fun teenage romance. It’s also the perfect movie to watch if you need a reminder that adulthood isn’t so bad after all.

8. It’s Complicated – Peacock

If you’ve ever been divorced, or have divorced parents, or just like a comedy of errors, this is the romantic comedy for you. It stars Meryl Streep as the ex-wife, Alec Baldwin as the ex-husband, and Steve Martin as the new flame. This movie not just hilarious, but it also portrays relationships in a way we’re not used to in the Rom-Com world. The characters are all older, this is not romance among 20 or 30-somethings like we’re used to. It also, as the title says, explores the complicated nature of family relationships, divorce, and post-divorce stuff. While that sounds intense, it’s really not. It’s all in the name of good fun.

9. Funny Face – Amazon

Audrey Hepburn shines as a bookshop worker turned fashion model in this 1950s classic. She travels to Paris for a big fashion show and finds herself questioning her journey and falling for a photographer. Between Hepburn’s gorgeous performance, the fashion, and the ever-magical Paris scenery, this movie makes even rainy days in quarantine feel fabulous. I highly recommend watching this movie in your best matching PJ set with a bottle of French-sounding champagne. That combination just feels so romantic and classy. Perfect for Valentine’s Day.

10. Mamma Mia! – Peacock

This is the story of a young woman who travels to her mother’s bed and breakfast in Greece to get married. She get’s a little more than she bargained for when she uncovers some juicy secrets about her mom’s past that throw a little wrench into wedding festivities. Meryl Streep again stars, and you just can’t go wrong with Streep. It’s also a musical based entirely on the works of ABBA. This one is great if you just need some happiness and a laugh.

11. Someone Great – Netflix

Someone Great is another one that just might stretch the boundaries of the Rom-Com genre just a little bit. When a young woman gets her dream job, her boyfriend of nine years breaks up with her, because it’s on the other side of the country. With her two best friends, she goes on a post-breakup adventure before her big move from New York to San Francisco. It’s a beautiful tale of modern female friendship that’ll leave everyone smiling.

12. When We First Met – Netflix

This is a just very cute movie. It’s a little cheesy, but isn’t that kind of what Rom-Coms are for? It’s a very classic style romantic film, and it will give you those warm fuzzies that these movies are kind of meant for. Adam DeVine is adorable as a guy who uses a magical photo booth to go back in time over and over again to the night he first met Avery, in an effort to make his dream girl fall in love with him.

13. Bride and Prejudice – Amazon

Okay, this is kind of an obscure pick but it’s so deeply worth it, so bear with me here for a second. This is an early 2000’s Bollywood take on Jane Austen’s Pride and Prejudice and it is marvelous. This is also one of my favorite movies of all time. At a wedding, a young Indian girl from a family of sisters meets a slightly pompous British guy visiting with his friend from university. It proceeds how the classic story does, but with truly gorgeous clothing and upbeat, and truly amazing Bollywood musical and dance numbers. The actors are incredible, it’s funny, it’s lighthearted, and it’s just so fun to watch. 10/10 recommend for Valentine’s Day viewing.

14. About Time – Netflix

This is definitely the most tear-jerking of the romantic comedies on this list, so be prepared for some tears. You’ve been warned. But if you need a good cry this Valentine’s Day, there is no better place to turn. Tim discovers that the men in his family can time travel, and he uses his newfound power to turn back the clock and win the girl of his dreams. This movie is romantic in a deeply moving way, and that’s what brings the tears.

Olivia Smith is a Senior Staff Writer at Grit Daily. Based in San Francisco, she covers events, entertainment, fashion, and technology. She also serves as a Voices contributor at PopSugar.

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