25 of the most swoon-worthy romance movies of all time

Heath Ledger and Julia Stiles at swing in a scene from the film '10 Things I Hate About You', 1999. (Photo by Buena Vista/Getty Images)
Heath Ledger and Julia Stiles at swing in a scene from the film '10 Things I Hate About You', 1999. (Photo by Buena Vista/Getty Images) /
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Pretty Woman

A love story between a hooker and a businessman isn’t normally something you think you’d call romantic, but with the right actors and a great script somehow it gets pulled off.

In Pretty Woman a prostitute and a wealthy businessman fall hard for one another, forming an unlikely pair. While on a business trip in L.A., Edward (Richard Gere), who makes a living buying and breaking up companies, picks up Vivian (Julia Roberts) on a lark (or so we hope, right?). After Edward hires Vivian to stay with him for the weekend, the two get closer, though neither is willing to admit it to the other. Edward spoils Vivian, treating her to fancy restaurants, taking her for the most epic makeover of all time, and bringing her to the opera in private jets. But things don’t go exactly as planned when Edward’s lawyer and friend (Jason Alexander) learns of her true profession and doesn’t like the change he’s seeing in Edward.

The movie is a modern take on the classic Cinderella story, and I swear that more women wanted to be sex workers that year than ever before.

The movie was originally set up to be a cautionary tale about sex work, and they were originally going to have Kit (Vivian’s roommate and friend) overdose. Glad they didn’t do that as the movie would have taken a pretty dark twist!

The absolute chemistry between Gere (swoon) and Roberts was so palpable they made a second movie together years later (Runaway Bride). If you watch Pretty Woman and then Runaway Bride back to back you might notice some Pretty Woman tributes hidden throughout the movie… go do it now!

Fun Fact: The film was wildly successful in the box office and saw the highest number of ticket sales in the U.S. ever for a romantic comedy, with Box Office Mojo listing it as the No. 1 romantic comedy by the highest estimated domestic tickets sold at 42,176,400, slightly ahead of My Big Fat Greek Wedding (2002) at 41,419,500 tickets.

Release date: March 23, 1990