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10 Romance Movies Like Pretty Woman That Are a Sure Thing

We want the fairy tale.

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  • Photo Credit: Buena Vista Pictures

When Pretty Woman hit theaters in 1990, the modern Cinderella tale about a sex worker who steals the heart of a wealthy businessman won over a legion of fans. More than 30 years later, it remains one of the greatest rom-coms.

Released just a year after Steel Magnolias, this openhearted love fable cemented Julia Roberts as “America’s Sweetheart” and a true Hollywood icon alongside A-list star Richard Gere. Director Gary Marshall was so impressed with the film's box-office success that he picked the couple to do it all again in Runaway Bride.

With the same director, stars, and similar meet-cutes, you can bet it made it onto this list of movies like Pretty Woman. If you love Vivian and Edwards's fairy-tale romance as much as we do, you’ll love these other films with just as much fashion, unlikely pairings, and big city backdrops.

Maid in Manhattan (2002)

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  • Photo Credit: Columbia Pictures

Jennifer Lopez plays Marisa Ventura, a struggling single mom who works at a ritzy Manhattan hotel and dreams of a better life for herself and her young son. A stroke of luck lands her in the company of Christopher Marshall, heir to a political dynasty, who mistakes her for a wealthy socialite.

After a magical evening together, the pair can’t deny the obvious sparks between them. But when Marisa’s true identity reveals itself, issues of class and social status threaten to separate them and destroy their fairy-tale love affair.

The Spectacular Now (2013)

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  • Photo Credit: Fox Searchlight

Sutter Keely is your average popular senior guy; he’s the life of the party and lives in the now with no actual plans for the future. But after being dumped by his girlfriend, Sutter has one too many drinks and blacks out on Aimee Finecky’s lawn.

Aimee, an introvert focused on school, couldn’t be more opposite from Sutter. As she dreams of her future, he lives in the delusion of a spectacular now, yet unexpected romance blossoms between them.

Runaway Bride (1999)

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  • Photo Credit: Paramount Pictures

Just like in Pretty Woman, Gary Marshall directs Julia Roberts and Richard Gere in this hilarious rom-com. With the band back together, Roberts plays Maggie Carpenter, a woman with a reputation for leaving her fiancés at the altar. Gere plays Ike Graham, a jaded newspaper columnist assigned to write a story on Maggie.

Without doing much research, Ike writes an offensive column, prints Maggie's name, and is surprised when she writes a hostile letter to the editor. After being fired for the falsified story, he heads to Maggie’s hometown in Maryland to write a fact-based report, hoping it’ll get him back in the business.

As he gets to know her, he realizes she’s not the cold-hearted runaway bride people made her out to be. Maggie’s been searching for love and acceptance and even with all his prying, Ike may be the guy to give her just that. 

Breakfast at Tiffany's (1961)

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  • Photo Credit: Paramount Pictures

When struggling writer Paul Varjak moves into a new apartment building, he becomes intrigued by his pretty, quirky neighbor Holly Golightly. Her dazzling lifestyle as a Manhattan socialite and escort confuses and fascinates him.

She flits through parties and social scenes with sophistication and charm, but when alone with Paul, the mask comes off, revealing a sweet and vulnerable creature. The reluctant lovers fall for each other, but their dark pasts threaten to get in the way of a happy ever after.

Sweet Home Alabama (2002)

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  • Photo Credit: Buena Vista Pictures

Melanie Smooter, played by Reese Witherspoon, is a southern belle who has reinvented herself as a New York fashion mogul. When her wealthy boyfriend proposes, it feels like all her dreams are finally coming true.

Except, there’s one problem - her estranged husband from back down south, who refuses to sign the divorce papers she sent years ago. To set things straight, she heads to the countryside to force him to finalize their divorce. But then her old home starts to tug at her heartstrings.

 Melanie discovers you can take the girl out of the south, but you can’t take the south out of the girl. She’ll have to choose between the life she always wanted and the one she can’t seem to forget.

You've Got Mail (1998)

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  • Photo Credit: Warner Bros.

Tom Hanks and Meg Ryan reunite their on-screen romance five years after Sleepless in Seattle. Meg plays Kathleen Kelly, a struggling boutique bookstore owner. Tom plays Joe Fox, owner of Manhattan's largest book chain whose enterprise could put every independent bookstore out of business.

The unlikely pair meet in an online chatroom and start an intense and anonymous love affair, despite already being in separate relationships. When Joe’s latest book superstore opens across the street from Kathleen’s store, she confides in her faceless friend for advice.

When Joe discovers his online love interest is his business rival, he struggles to choose between his work's mission and his heart's desire. 

Notting Hill (1999)

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  • Photo Credit: Universal Pictures

Julia Roberts and Hugh Grant are as brilliant as ever in this late 90s classic. Roberts basically plays herself as Anna Scott, a glamorous American film star shooting a movie in London. Grant plays a down-to-earth bookstore owner in Notting Hill.

On one fateful day, Anna walks into William's little bookshop, and something about him catches her eye. Maybe it’s his kindness and the laid-back lifestyle he lives. William falls for her too, and the pair’s chance encounter blossoms into a full-blown love affair.

Being together is more complex than the simple attraction they have to each other. Their individual lives pull them in all different directions as they struggle to make things work.

She's All That (1999)

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  • Photo Credit: Miramax Films

High school dreamboat Zach Siler’s perfect world comes crashing down when his girlfriend dumps him for a reality tv-star. With his popularity on the line, he makes a risky bet that he can turn any girl, no matter how geeky, into a prom queen.

Enter Laney Boggs, a nerdy outcast who doesn’t have time for the frills of high school gossip and boys. She longs for an art school scholarship and isn’t about to let anything distract her. Except maybe Zach, whose boyish charm slowly wears her down.

The weeks leading to prom fly by, and an unexpected friendship grows between them. As Zach attempts to up Laney’s popularity status, he instead finds himself falling for the real her. But Zach’s secret motives, if revealed, threaten to destroy any chance of romance between the two.

The Wedding Date (2005)

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  • Photo Credit: Universal Pictures

In true Pretty Woman fashion, Kat Ellis hires escort Nick Mercer to accompany her to her sister’s wedding, where her ex-boyfriend is the best man.  

Nick has good looks and a keen insight into human behavior, a valued trick of his trade. Over the wedding weekend, he assumes various roles, including therapist for the bride, potential son-in-law for the father, friend for the groom, and the center of attention for all women. 

As Nick and Kat’s fake relationship progresses, it transforms into something surprising and offers her a chance at love again.

Ten Things I Hate About You (1999)

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  • Photo Credit: Buena Vista Pictures

This late 90’s quintessential teenage rom-com is a modern take on Shakespeare’s Taming of the Shrew. In this story, Bianca Stratford is in a dilemma. Her dad’s strict rules forbid her from dating until her rebellious, boy-hating older sister Kat finds her own boyfriend.

When Bianca catches the eye of new student Cameron, they devise a plan to set Kat up with Patrick, another rebel who may just be the match for Kat. Patrick agrees to their scheme, and after several failed attempts to court her, he lands himself a date. But he never imagined actually falling for Kat.

The more time they spend together, Kat sheds another layer of her hard exterior, revealing a sweet, vulnerable side. But like all Shakespeare novels, tragedy looms, as Patrick’s secret deal could be exposed to Kat at any moment.

Featured Still from "Pretty Woman" via Buena Vista Pictures