35 Rom-Coms Every Woman Should Watch Before She Turns 30

Cue the makeover montage!

Romantic comedies: you love them or you tolerate them, but they're always good for some light entertainment and a life lesson or two. (Okay okay, and sometimes a few tears.) Here, the best and most classic rom-coms to watch before you break 30—especially since the big 3-0 is such a rom-com trope in and of itself.

1 of 35
The Big Sick

Romances are always sweeter when they're based on real life stories, which is why this new rom-com from Silicon Valley's Kumail Nanjiani is such a breath of fresh air. It grounds the typical rom-com tropes in a time of Uber and dating apps, portraying an interracial romance between stand-up comic Kumail (played by himself) and his wife Emily (played by indie rom-com queen Zoe Kazan). They face their biggest challenge when Emily develops a sudden sickness that lands her in a coma.

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2 of 35
The 40-Year-Old Virgin

Steve Carrell plays a sweet 40-something who has zero game in this Judd Apatow movie. When his co-workers discover that he's still a virgin, they try to help him work on his dating skills.

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3 of 35
Some Like it Hot

Marilyn Monroe plays a member of a traveling jazz band who believes she's fallen in love with a millionaire, when in fact she's being duped by one of her fellow band members (a man on the run who's pretending to be a woman). Some Like It Hot features one of the steamiest kisses in film history and lots of great Marilyn Monroe song numbers.

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4 of 35
Heartbreakers

This rom-com has one of the most hilarious concepts: A mother and daughter play two con-women who scam wealthy men out of money. Sigourney Weaver plays the mother who hooks the men, and the daughter (played by Jennifer Love Hewitt) plays the one who elicits an affair with them to produce a divorce check. Their next heist goes awry when one of their victims comes back to catch them in the act.

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5 of 35
How To Lose a Guy in 10 Days

A lady mag journalist wants to take on more serious pieces, so her boss assigns her one last fluff piece as a final challenge: a story on how to lose a guy in 10 days. She uses all of the behavior men have been calling women "crazy" for for ages, but ends up falling for the guy she's trying to get rid of. What she doesn't know is that he's taken a bet that he can make her fall in love with him, so it's a classic conflict of interests.

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6 of 35
La La Land

This modern musical directed by the very young Damien Chazelle (of Whiplash fame) re-unites Emma Stone and Ryan Gosling in this magical love story set in L.A. about ambition, integrity, and timing that has enough dance numbers and beautiful duets to melt you into your seat.

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7 of 35
Moonstruck

The full moon sometimes makes us do crazy things—or, at least, that's what we'd like to blame—which is the central theme of this film about a widow (played by the fabulous Cher) who travels with her fiancé to Sicily to meet his family. She ends up falling for his baker brother (Nicolas Cage), while her father and mother engage in extra-marital affairs, and the romantic hijinx won over critics who awarded the film three Oscars, including a Best Actress award for Cher.

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8 of 35
The Philadelphia Story

A rom-com for the ages, this classic from 1940 stars Carey Grant and Katharine Hepburn as a married couple on the rocks. Hepburn plays Tracey Lord, a socialite who attempts to remarry after throwing out her ex-husband (Grant), until he shows up to her nuptials with an investigative journalist who's clued in on her dark family history.

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9 of 35
My Best Friend's Wedding

No movie captures the frustration of being in love with your best friend quite like My Best Friend's Wedding, a sublime rom-com starring '90s screen queens Cameron Diaz and Julia Roberts. Roberts plays a 27-year old food critic who realizes she's in love with her best guy friend when he announces he's getting married to a college-age student, and decides to subtly sabotage their wedding.

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10 of 35
The Artist

A truly one-of-its kind movie, this modern oldie won the Oscar for Best Film in 2012, though it was directed in all black-and-white with no dialogue to mimic the style of silent films before "talkies" came around. A successful actor takes a young ingenue dancer under his wing in the midst of the creation of talking pictures, only to watch her career eclipse his in a big way. The dancing and dynamics between actors are fantastic, and it's a must-see for people swept away by the romance of La La Land.

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11 of 35
Sixteen Candles

No one plays angsty teens quite like Molly Ringwald and she's at both her eye-rolliest in this teen flick about a wallflower who has to fend off her crazy extended family that's in-town for her sister's wedding. All of this aside, she's pining for the most popular boy in school (the dreamy Jake Ryan) who's caught wind of it and wants to reach out.

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12 of 35
Lars and the Real Girl

It's not exactly your typical rom-com humor, but watching Lars and the Real Girl, you experience so many different life realities: loneliness, the hope of unconventional love, empathy, and even some subtle laughs. An almost unrecognizable Ryan Gosling plays a man who falls in love with a doll he orders on line, who his brother and sister-in-law tend to as if she were human.

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13 of 35
How to Lose a Guy in 10 Days

It's the perfect scheme. A young lady mag journalist wants to write more serious pieces and lands the perfect piece to prove herself: "How to Lose a Guy in 10 Days." She has to pick up a dashing ad executive (a very underrated Matthew McConaughey) and play the whole "crazy girlfriend" shtick to report about it. What she doesn't realize is that he's vying to win a bet, too, that he can make her fall in love with him in 10 days.

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14 of 35
Ruby Sparks

This indie rom-com captures a writer's daydream come to life, as the character he lusts for somehow gets magicked into being. Everything he writes becomes reality until he realizes the dangers of having a girlfriend who has no free will. There are so many great things about this movie, from its commentary on the male gaze to the excellent chemistry between IRL couple Zoe Kazan and Paul Dano.

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15 of 35
Crazy, Stupid, Love

Hopefully there'll be many more romantic movies to come from Ryan Gosling and Emma Stone, because they're irresistible as a pair. Gosling plays a ladies' man who falls for the deadpan, unsinkable Hannah (Stone), while he's also trying to help a hapless divorce (played by Steve Carrell) get his manly groove back.

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16 of 35
13 Going on 30

All Jenna Rink wants to be is "30, flirty, and thriving" until she actually gets what she wishes for. The bewilderment of being 13 in a 30-year-old's body is played pretty much perfectly here by Jennifer Garner, and this film captures the exact moment where the world truly fell in love with Mark Ruffalo.

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17 of 35
TiMER

If you've ever mulled over the question of what it means to have a soulmate, TiMER lets you imagine what it would be like to wear a futuristic device that counts down to the exact moment when you'll meet your "one." The film captures the anxiety of growing older without a concrete romantic prospect in sight (get used to it!), and debates the idea of living in the moment versus waiting for your prince charming.

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18 of 35
Bridget Jones' Diary

The hilarious and uncensored Bridget Jones (played by Renée Zellweger) forever has our loyalty as a news anchor caught in a love triangle with her boss and her childhood friend Mr. Mark Darcy (actually modeled off the brooding Pride & Prejudice suitor). The British humor is pitch perfect and glorifies the idea of being unapologetically yourself, flaws and all.

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19 of 35
10 Things I Hate About You

One of the most clever teen comedies of all time, 10 Things I Hate About You is a classic for its whip-smart script and hilarious camaraderie between the actors (see a young Heath Ledger and Joseph Gordon-Levitt). Not to mention, all the signature rom-com moments, from epic dance and song scenes (honestly, it's worth watching just to see Heath Ledger's immortal dance number with a marching band) to public declarations of love.

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20 of 35
Clueless

Obviously you have seen this, so you don't need to read a description. (Okay okayyyy if somehow you haven't, here you go: This modern update of Jane Austen's Emma sees a California high-school girl as she balances her social life, bettering herself and others, and keeping up her expansive closet.)

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21 of 35
Harold and Maude

One of the darkest and most offbeat of romantic comedies, Harold and Maude is about a morbid young boy with a penchant for faking his own death who falls in love with a carefree 80-year-old woman who teaches him a new appreciation for life.

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22 of 35
Silver Linings Playbook

Jennifer Lawrence. Bradley Cooper. Attitude. Dance Competition. Any questions?

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23 of 35
Annie Hall

Woody Allen is his signature neurotic self in this New York-based comedy about the ups and downs of one relationship over the course of several years.

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24 of 35
Pretty Woman

Clearly this is a requirement. Julia Roberts is epic in this movie about a wealthy businessman who becomes smitten with a prostitute he hires on a whim.

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25 of 35
The Wedding Singer

Adam Sandler and Drew Barrymore play a waitress and a wedding singer who are engaged to the wrong people, until they have the good fortune to meet each other.

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26 of 35
When Harry Met Sally

This quintessential rom-com begs the question "can guys and girls ever truly be friends?" Rom-com queen Meg Ryan goes toe-to-toe with Billy Crystal in a story about an 11-year friendship between two friends who try to keep the line between friends and lovers separate.

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27 of 35
Breakfast at Tiffany's

Audrey Hepburn plays the ultimate "woman of the world who doesn't want to settle down" in this classic '60s film about a writer who falls in love with his society-girl neighbor. Her entanglements become his entanglements as the pair start to get more involved.

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28 of 35
There's Something About Mary

A story in which a teenage dirtbag lands his dream girl for the senior prom, and then...mishaps occur. This classic comedy follows him several years later as he gets reunited with her and tries to win her back.

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29 of 35
Obvious Child

Though abortions aren't typically the stuff of comedy gold, writer/director Jillian Robespierre frames this hilarious and heartwarming comedy around a standup comic's accidental pregnancy via a one-night-stand. The anxiety and odd humor of the film makes this one of the most groundbreaking and relatable films about pregnancy and relationships in a long time.

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30 of 35
Enough Said

Two single parents come together in this sweet comedy about learning to love someone past the honeymoon phase, even after you've discovered all their little flaws. The banter between Julia Louis-Dreyfus and James Gandolfini (who ditches his mob boss character for a much softer role—his last, *sobs*) is golden, and the casting is spot-on.

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