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50 Best Romantic Comedies That Are Worth the Watch Every Single Time

You'll laugh while feeling hopelessly in love!

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best romantic comedies

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There is truly never a wrong time for a good romantic flick. But for those who don't feel like spending their time watching typical sad romance movies or popular Valentine's Day movies, a good middle ground is a classic rom-com! Can you name anything better than being able to feel hopelessly in love with the protagonists, while also letting out a few snarky laughs? Didn't think so! We've rounded up the best romantic comedies of all time that somehow never get old, no matter how many times we revisit them. What can we say—they had us at hello!

If your evening to-do list includes a much-needed escape into a romantic comedy, then we’re happy to provide you with this ultimate guide to the funniest love stories out there. These picks feature all the rom-com greats, including Molly Ringwald, Gabrielle Union, Meg Ryan, Julia Roberts, and plenty of Tom Hanks and Richard Gere, too. These films also span decades, meaning there’s something nostalgic for an at-home date night with your sweetheart, and more modern options that pickier kids or teens might actually enjoy. Of course, the best possible way to enjoy these flicks might be to have a quiet night to yourself in front of the TV, so you can watch John Cusack hold up his boombox in peace. What could be more romantic than that?!

1

Happiness for Beginners

Happiness for Beginners
Credit: Netflix

Divorce can be hard, that's for sure. When this schoolteacher finds herself in the midst of one, she decides to sign up for a group hike to clear her mind. The exact opposite happens when she meets a charming man (played by Yellowstone's Luke Grimes), who has her mind going a million different places.

2

Love Again

Love Again
Credit: Netflix

If a few cameos by Céline Dion isn't enough to convince you, then read about the plot: A woman deals with the loss of her fiancé by texting him everyday after his death. Little does she know, a new man now has his phone number—and he's reading every single one, falling in love with her from a distance. Will he rise up the courage to reveal himself to her?

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3

Red, White & Royal Blue

Red, White & Royal Blue
Credit: AMAZON

The president's son and a young Britain prince don't exactly like each other. In fact, they have this unspoken beef that accelerates every time they see each other in person. But if there's one thing about enemies, it's that they sometimes turn into... you can see where this is going!

4

Down With Love

Down With Love

Barbara doesn't need a man and she swears by it. She's even created an entire empire based off that fact, influencing women everywhere to feel the same! But what happens when Catcher, a scheming male writer, tries to challenge this by making her fall in love with him? Will she fall into his trap?

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5

Some Kind of Wonderful

Some Kind of Wonderful
Credit: AMAZON

Talk about a love triangle! Let's get this teen-romance debacle straight: Keith begins dating Amanda. Amanda's ex-boyfriend is now jealous. Keith's best friend, Watts, now realizes she has feelings for him—which didn't occur to her until after he was no longer single. Phew!

6

Because I Said So

Because I Said So
Credit: AMAZON

Diane Keaton plays a mother who would do anything for her daughters. That includes secretly creating an online dating ad for her youngest, Milly (Mandy Moore), who doesn't have the greatest luck with men.

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7

Emma

Emma
Credit: AMAZON

Jane Austen fans know that the acclaimed author is a genius at creating the most hilarious, descriptive love stories. Emma is no exception, and this recent retelling of the story about happy endings (and what it takes to experience one) is definitely worth the watch.

8

Picture Perfect

Picture Perfect

Kate (Jennifer Aniston) is rightfully upset that the sole reason she doesn't get a promotion is because of her shaky love life. So, she does what anyone else would do, and picks a random person to be her fake fiancée. She didn't plan on actually falling in love with him, but would that be so bad?

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9

The Wedding Date

The Wedding Date
Credit: AMAZON

Random wedding dates are the obvious way to make your ex-jealous. That's if everything goes according to plan... which is never the case in movies. (It just makes for a more entertaining watch!)

10

The Shop Around the Corner

The Shop Around the Corner
Credit: AMAZON

If you're a fan of You've Got Mail, then you'll love the movie that inspired it all! Watch this classic about a pair of pen pals who ultimately fall in love once they meet each other in person.

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11

The Wedding Planner

The Wedding Planner
Credit: AMAZON

Mary (Jennifer Lopez) is the best wedding planner in the business. Too bad she hasn't had much luck planning one of her own. That all changes when she meets a handsome doctor (Matthew McConaughey) in the most embarrassing way possible.

12

Set It Up

Set It Up
Credit: Netflix

Two entry-level assistants at a big-corporate business are feeling a little swamped with work. So, they decide to nonchalantly get their bosses to start dating with the hopes of this lessening their actual workload. Their plan may have them both falling in love!

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13

He's Just Not That Into You

He's Just Not That Into You

Nine people. All different love stories. Plus, a striking, all-star cast! Is there anything else you could ask for in a romantic comedy?!

14

Always Be My Maybe

Always Be My Maybe

A couple who broke up years ago find themselves crossing paths all this time later. They *think* they feel a connection brewing up once again, but the only caveat is that their lives are so different now. One is a super-star chef while the other is an up-and-coming musician.

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15

Two Weeks Notice

Two Weeks Notice
Credit: AMAZON

Sandra Bullock and Hugh Grant are hilarious, witty, and chemistry-bound in this story about a lawyer who ends up falling in love with her arrogant boss. It may not have been love at first sight, but that hardly matters in our favorite flicks!

16

Ghost

Ghost
Credit: AMAZON

It's the iconic love story between a ghost and the love he left behind. Whoopi Goldberg took home an Academy Award for her role as the psychic in the film.

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17

She's the Man

She's the Man
Credit: AMAZON

Okay, sit tight for this one. A teenage girl (Amanda Bynes) poses as her twin brother at his boarding school. She ends up falling for her roommate (Channing Tatum), but he has his eye on someone else. Then, things really take a turn when the twin brother returns to school.

18

The Big Sick

The Big Sick
Credit: AMAZON

A comic and a grad student fall in love, but when their cultures clash, it becomes a bit complicated. It takes a mysterious illness to finally bring their families together.

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19

Spoiler Alert

Spoiler Alert
Credit: AMC

This is a heartwarming and heartbreaking story of two men who fall in love. All goes well, until one of them becomes deathly ill.

20

The Parent Trap (1998)

The Parent Trap (1998)
Credit: AMAZON

Two mischievous twins decide to secretly switch places in order to reunite their separated parents. Will their scheme work?

Headshot of Megan Stein

Megan Stein is the executive editor for The Pioneer Woman, and oversees entertainment, features, and news for the website. Whether it's catching up on the latest true crime podcast, or re-watching the best '80s movies for the zillionth time, she's always here to talk about anything and everything relating to pop culture.

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