5 Romantic Comedies That Almost Had Very Different Endings

Meg Ryan and Billy Crystal in When Harry Met Sally
(Image credit: Columbia Pictures)

The Pretty in Pink kiss in the parking lot, Harry running through Washington Square Park to profess his love to Sally, and Fever Pitch showing the Red Sox breaking the “Curse of the Bambino” will forever go down as some of the most memorable endings in romantic comedies. However, as iconic as those final moments are, each of those movies, and a couple of others, almost looked entirely different before they premiered on the big screen. 

But, how were each of those all-time great romantic comedies supposed to end? Funny you should ask, because we’re about to break down a handful of titles that almost had very different endings that either never left the pages of the screenplay, were cut after poor test screenings, or in the case of the 2005 Jimmy Fallon and Drew Barrymore movie, were changed by one of the most electric moments in modern sports history. Before we get too far, please note there are major spoilers for each of the five movies being discussed…

Billy Crystal and Meg Ryan in When Harry Met Sally...

(Image credit: Columbia Pictures)

When Harry Met Sally… (1989)

Considered one of the best romantic comedies of all time, When Harry Met Sally… ends with the titular characters (played Billy Crystal and Meg Ryan) reuniting and professing their love for one another at a New Year’s Eve party after their awkward sexual encounter a few months earlier. As the partygoers around them count down until the ball drops, the pair have a heated conversation that ends with Harry telling Sally, “I came here tonight because when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.” 

After that, the movie cuts to the final interview segment, only this time instead of older married couples, it’s Harry and Sally talking about their wedding that took place just three months after the party. However, this wasn’t the original ending, as Rob Reiner told PeopleTV (via EW) in 2018:

I was single for ten years and making a mess of my personal life, in and out of relationships and not being able to making anything work. The first draft of the script — or the draft we were going to shoot — Harry and Sally weren’t going to get together. They meet each other years later and then walk separate ways.

So, why the big change? Well, Reiner met his wife, Michelle Singer, while making the movie and was inspired to come up with a happier ending with screenwriter Nora Ephron.

Julia Roberts eating food in a robe in Pretty Woman.

(Image credit: Buena Vista Pictures)

Pretty Woman (1990)

Garry Marshall’s 1990 landmark romantic comedy, Pretty Woman, ends with Edward Lewis (Richard Gere) climbing out of the moonroof of his limousine and climbing up Vivian Ward’s (Julia Roberts) fire escape to show his commitment to the woman he loves. However, the film’s original ending, much like the rest of J.F. Lawton’s initial script, was much darker and didn’t have that fairytale ending that resulted in the movie making more than $460 million at the box office.

When speaking with Patricia Arquette as part of Variety’s Actors on Actors series, Roberts explained that the original ending in the script saw Vivian being thrown out of the limo into a dark alley with nothing more than the money being thrown on top of her. Diane Lane, who was up for the role at one point, also spoke about the darker tone of Lawton’s screenplay during an appearance on Watch What Happens Live with Andy Cohen, stating that the eventual comedy hit was “Disney-fied” before it was released.

My Best Friend's Wedding

(Image credit: Sony Pictures Entertainment (SPE))

My Best Friend’s Wedding (1997)

Seven years after Julia Roberts got her man in Pretty Woman, the A-lister appeared in another box office smash hit romantic comedy with 1997’s My Best Friend’s Wedding. The movie centers around New York City food critic Julianne “Jules” Potter as she realizes she’s in love with her best friend, Michael O’Neal (Dermot Mulroney), just before he’s set to marry Kimmy Wallace (Cameron Diaz). The story ends with a heartbroken yet understanding Jules moving on at the wedding before having a dance with her friend George Downes (Rupert Everett) who’s a surprise guest.

Though not as drastically different as other movies on this list, the original ending did have one minor change that reportedly was not a hit with test audiences, according to director P.J. Hogan. In a 2017 EW interview, Hogan revealed that Jules met a new guy at the wedding instead of having a meaningful dance with George. A few months after principal photography wrapped, Roberts was back on set (with a wig) to film the new ending.

Drew Barrymore and Jimmy Fallon in Fever Pitch

(Image credit: 20th Century Fox)

Fever Pitch (2005)

The Farrelly Brothers’ 2005 adaptation of Nick Hornby’s Fever Pitch has an ending that coincides with one of the biggest moments in modern sports history: the 2004 Boston Red Sox World Series victory. The movie ends with Ben Wrightman (Jimmy Fallon) and Lindsey Meeks (Drew Barrymore) kissing on the field at Busch Stadium in St. Louis after the Red Sox swept the Cardinals to break the “Curse of the Bambino.” This wasn’t how the movie was supposed to end, but no one knew Boston history was about to be made.

In November 2004, after Boston secured its first World Series title in nearly a century, EW reported that the original plan was to have the scene of Lindsey running on the field during a Red Sox playoff game serve as the final scene, but fate had other plans. After production had wrapped, the Farrelly Brothers, Fallon, Barrymore, and a camera crew went to the deciding Game 4 of the World Series to capture the epic moment and completely change the final act of the movie.

Molly Ringwald in Pretty in Pink

(Image credit: Paramount Pictures)

Pretty In Pink (1986)

And then there is Pretty in Pink, John Hughes’ 1986 teen romantic comedy starring Molly Ringwald as high school senior Andie Walsh, as she falls head over heels for Andrew McCarthy’s Blane McDonough, who strings her along for most of the movie. That all changes at the end, when Blane admits to being a jerk and professes his love for Andie at senior prom as the movie draws to an end. However, the film originally had a different ending, one that saw Andie end up with her best friend Duckie Dale (Jon Cryer) before a test audience booed it, as director Howard Deutch told CinemaBlend in 2020:

The original ending was Duckie and Molly ended up together. And the audience booed. And so we all had a heart attack, and had to reshoot. And John figured out how to change it so that Andrew came alone to the prom, and then Duckie sacrificed his love, and Molly and Andrew could be together.

Writer John Hughes was quick to make to make the necessary changes to the script, and the film has since gone down as one of the most iconic of the “Brat Pack” era.

Each of these five romantic comedies were changed in some shape or form before they were finally released. Who knows, maybe we’ll find out the same thing about some of the 2022 new movie releases at some point in the future.

Philip Sledge
Content Producer

Philip grew up in Louisiana (not New Orleans) before moving to St. Louis after graduating from Louisiana State University-Shreveport. When he's not writing about movies or television, Philip can be found being chased by his three kids, telling his dogs to stop yelling at the mailman, or yelling about professional wrestling to his wife. If the stars properly align, he will talk about For Love Of The Game being the best baseball movie of all time.