With Valentine’s Day around the corner, it’s time to look back at some of the best rom-coms of all time to get you in the romantic mood. Whether you’re planning a cute movie date or planning a cozy night with your friends, these are some of my personal favorites that just never get old.
The romantic comedy might be a lost art in the modern cinema world, but looking back on the past 20 years, there are dozens of cozy classics from the past to fall in love with this romantic season.
Not every rom-com is a hit, but stick on one of these ten movies and you are guaranteed to have a Valentine’s Day like no other.
1. Crazy, Stupid, Love
First up we have Crazy, Stupid, Love. It all starts as Cal’s wife asks for a divorce and his entire life goes downhill. One night, as Cal is wasting away at a bar, telling his whole life story to anyone who will listen, he is approached by Jacob, who happens to be a professional ‘ladies man’. Jacob decides to take Cal under his wing and help him enter the world of dating. But as Cal becomes more successful in the dating pool, he realizes how much he actually misses his wife.
The plot thickens as more characters and storylines come into play, but you won’t know until the very end how they all intertwine. The ending alone is enough for you to desperately need to watch this movie.
IMDb: 7.4/10
Where to Watch: Netflix
2. 10 Things I Hate About You
This Taming of the Shrew retelling is a perfect enemies-to-lovers rom-com. 10 Things I Hate About You, starring Heath Ledger and Julia Stiles, follows the story of Kat Stratford as Patrick Verona tries to date her, even if she is completely undateable.
But little does she know that he’s being paid by the boy who has a crush on Kat’s little sister. Heath and Julia have unmatched chemistry that really brings the film to life. This is a movie you can watch on repeat — it’s just that good.
IMDb: 7.3/10
Where to Watch: Disney+
3. Crazy Rich Asians
What the internet has proclaimed the perfect airplane movie, Crazy Rich Asians is a flawless romantic comedy that will leave you wishing there was a sequel.
As Rachel Chu and her boyfriend Nick travel to his best friend’s wedding in Singapore, Rachel soon realizes that Nick hasn’t been truthful about his upbringing. She learns that Nick’s family is unfathomably wealthy and is the most eligible bachelor in the family empire. But being thrown into the spotlight isn’t the only thing she has to worry about. The biggest threat to their relationship happens to be the head of the Young Empire: Nick’s terrifying mother.
IMDb: 6.9/10
Where to Watch: Netflix
4. Notting Hill
When famous American actress Anna Scott walks into William Thacker’s travel bookshop, he has no idea it would be the beginning of a romance that is only ever seen in the movies. Even if they want to be with each other, Anna and William must maneuver radically different lifestyles.
Notting Hill is one of the best 90’s rom-coms, filled with classic British comedy and heartfelt moments that will leave you wishing the movie star of your dreams would stumble into your life.
IMDb: 7.2/10
Where to Watch: Netflix
5. How To Lose A Guy In 10 Days
As Andie Anderson tries to write a column on how to lose a guy in 10 days, she meets Ben Berry to test out the experiment. Yet Andie doesn’t know that Ben has been challenged to make a woman fall in love with him in just 10 days. The two are completely oblivious to each other’s true motives, which makes for some absolutely ridiculous moments as the two try to date each other.
How to Lose a Guy in 10 Days stars Matthew McConaughey and Kate Hudson. The two have amazing chemistry throughout the film, even when they are trying to drive each other crazy.
IMDb: 6.5/10
Where to Watch: Netflix
6. The Princess Bride
On top of being a rom-com, The Princess Bride is a classic satirical fantasy. The story follows Princess Buttercup as she comes to terms with the death of her true love, Wesley. But little does she know, he is alive and well as he swoops in to save her from a kidnapping.
The two lovebirds travel through the fictional kingdom of Florin as Buttercup’s betrothed, Prince Humperdinck, follows close behind. To anyone searching for the perfect lighthearted fairytale to watch this Valentine’s Day, you must give this movie a shot.
IMDb: 8.0/10
Where to Watch: Disney+, Prime Video
7. The Proposal
Anyone who loves a faking dating trope must see The Proposal. Margaret Tate, played by Sandra Bullock, is a well-known book editor trying to find a solution to getting deported. Her unlucky assistant Andrew, played by Ryan Reynolds, gets dragged into a ruse as the two pretend to be engaged. As they try to fake it for their coworkers and families to believe, their plans fall apart when the feelings become real.
IMDb: 6.8/10
8. About Time
About Time has a unique spin when it comes to time travel. The blooming romance between characters Tim and Mary begins after his father tells him the family secret: the men in the family can travel through time. As Tim acquaints himself with his new gift, he uses time travel to win Mary’s heart.
You get to travel through Tim’s life as he discovers the true meaning of life. But don’t be fooled. This may be a romantic comedy, but don’t be surprised if you shed a tear or two.
IMDb: 7.8/10
Where to Watch: Prime Video, Netflix
9. Sixteen Candles
Have you ever imagined what it would be like to have everyone in your family forget your birthday? Well, Samantha knows exactly what that’s like. When everyone forgets about Sam’s 16th birthday, she goes to school wishing that the hottest boy in school, Jake Ryan, would at least notice her existence. But the only boy in school to notice her is nerdy boy Ted, who tries everything to get Sam to like him.
Sixteen Candles is a chaotic 80’s classic that is perfect for any teenager who dreams of having that high school sweetheart ending.
IMDb: 7.0/10
Where to Watch: Netflix
10. Valentine’s Day
Lastly, we have the iconic classic Valentine’s Day. This 2010 comedy walks you through multiple interconnected love stories in Los Angeles.
Not only does this movie have a hilarious plotline, but it has one of the most recognizable casts, including actors such as Bradley Cooper, Jamie Foxx, Julia Roberts, Anne Hathaway, and Ashton Kutcher. Even global popstar Taylor Swift makes an appearance, giving us a hysterical performance as the clingy lovesick girlfriend.
This film shows every kind of love that should be celebrated on Valentine’s Day and will make the holiday even more sappy when you realize how many people actually do love you.
IMDb: 5.7/10
Where to Watch: Apple TV, Prime Video
