10 Timeless Romantic Comedies You Won’t Be Able To Stop Watching

Since someone asked, here are my 10 most favorite romantic comedy films to date! This is in no particular order, of course, because that would be too hard already.

1. Little Manhattan (2005)

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“The truth is, there’s gonna be other girls out there. I mean, I hope. But I’m never gonna get another first love. That one is always gonna be her.”

Because honesty is the best policy, I will admit that the reason Little Manhattan made it to my list is mainly because I’m a sucker for the idea of first love. And first love here is portrayed in the most raw and unadulterated form possible as it is told from a perspective of an 11-year-old boy.

2. What Happens in Vegas (2008)

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“We got robbed—and all they took was the door!”

(I laugh a little too loudly on the inside everytime I recall that line.)

Ashton Kutcher and Cameron Diaz – casting them alone in one rom-com guaranteed What Happens in Vegas to be a hit already. Their comedic chemistry lights me up whatever my mood is. And I can honestly say that because of that, this has been one of my most rewatched movies ever. I just enjoy watching them fight over and over again in the most silly—and even brutal—ways. Oh and not to forget their personal sidekicks who are both quite a character themselves!

3. Never Been Kissed (1999)

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“Someone once told me that to write well, you have to write what you know…”

Never Been Kissed is one of those movies that I fell in love with as a kid, and so it appears impossible to unfavorite it anymore. Perhaps, I will always think of Josie Grossie as my kind of heroine, whose voice is outstanding and well-meaning and who happens to have a pen, too, that goes perfectly with it.

4. 10 Things I Hate About You (1999)

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“But mostly I hate the way I don’t hate you. Not even close, not even a little bit, not even at all.”

10 Things I Hate About You is brilliant in all sorts of ways. The cast alone is a beauty. Their overall chemistry is just so wonderful and unique. The movie has a lot of very quotable quotes, too, which could even be better than those of Mean Girls. Its soundtrack also wins it for me, as it’s one of the few OSTs that I still go back to even until today. And Heath’s field performance of Can’t Take My Eyes Off You? Classic! It may have caused me to decide at once that Heath was the most charming and beautiful man alive. (The last word breaks my heart.)

5. Sabrina (1954)

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“I’ve decided to be sensible and tore up his picture. Please mail me some Scotch tape.”

Four Oscar wins and seven nominations, how can Sabrina not make it to this list? Audrey Hepburn on her own already makes this black and white film more than just a pleasant watch. And not to forget her role’s unintentionally funny antics due to her untamed naivety before Paris! This movie is just so fascinating to watch, especially for girls who’ve experienced what it’s like to fall madly (literally) infatuated with a guy who may or may not recognize their existence.

6. 13 Going On 30 (2004)

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“I love you, Matt. You’re my best friend.”

This spot is initially for My Best Friend’s Wedding but I realized soon enough how much I love this one more. I love 13 Going On 30 because it’s so sincere in the truths it wants us to think of. And, of course, Matt and Jenna are just so perfect for each other. Best friends since childhood and meant to be together forever!

7. 500 Days of Summer (2009)

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“Look, I know you think she was the one, but I don’t. Now, I think you’re just remembering the good stuff. Next time you look back, I really think you should look again.”

I love 500 Days of Summer as it exposes some of the cracks in almost every couple’s relationships, as well as the cracks found in the head of every person in love. Let it make us better instead of bitter.

8. Some Kind of Wonderful (1987)

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“You break his heart, I break your face.”

Not the John Hughes film you were expecting? Hehe. Some Kind of Wonderful is another one of those movies where the guy protagonist goes after the girl of her dreams, and in doing so, finds himself also falling in love with the girl he’s known forever – his best friend. Typical plot but this movie still stands out for me, for reasons I myself can’t pinpoint exactly.

9. Juno (2007)

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“As far as boyfriends go, Paulie Bleeker is totally boss. He is the cheese to my macaroni. And, I know that people are supposed to fall in love before they reproduce, but… I guess normalcy isn’t really our style.”

Juno could be one of the most adorable protagonists there ever was, but I’m not sure we’d get along if she existed in my world, as she may be too rad to like a silly me. (How sad!) But anyway, I didn’t love this movie the first time I saw it as much as I did after how many rewatches.

What I like about Juno (the movie, not the character)? Well, like I said, the very witty Juno (the character and not the movie) and the rest of the characters including the awkwardly attractive Paulie Bleeker and Juno’s parents whose coolness lies in their uncoolness. Other factors include the brilliant exchange of lines pretty much all throughout the movie, the setting of it all, and the soundtrack which is a little too perfect for the movie. <3

10. Bridget Jones’s Diary (2001)

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“I’m still looking for something more extraordinary than that.”

What makes Bridget Jones irresistible is how she’s still incredibly funny and entertaining in spite of whatever depressing mess she’s in. It’s her ability to not take herself seriously in serious situations that causes me to adore her with such great passion. And it looks to me that it’s also the same reason why two great-looking guy eventually find themselves falling for her. It’s just that one of them ends up becoming nothing but a lesson for her to start shooting for the extraordinary.