Twenty-three years ago, Andie Anderson climbed into a taxi believing she was leaving New York — and Benjamin Barry — behind.

Then Ben came racing after her on a motorcycle.

It was exactly the kind of ending audiences expected from a great early-2000s romantic comedy: the misunderstanding had exploded, both sides had admitted their deception, the couple had discovered their feelings were real, and one grand gesture was all it took to send them toward happily ever after.

For more than two decades, that was where How to Lose a Guy in 10 Days left Andie and Ben.

Now Paramount is preparing to ask a much more complicated question: What happened after they stayed together?

A sequel to the 2003 romantic comedy is officially in early development at Paramount, with Kate Hudson attached as a producer alongside Stacey Sher. The project is still looking for a screenwriter, and no cast has formally been attached. The intention, however, is to find a version of the story that could bring Hudson and Matthew McConaughey back as Andie and Ben.

That distinction matters.

This is not yet a finished screenplay with Hudson and McConaughey signed and a production date on the calendar. It is a developing sequel whose biggest challenge may be finding a reason for these characters to return at all.

And that problem is far more interesting than simply recreating the love fern.

The original movie, released on Feb. 7, 2003, was built around two perfectly incompatible professional schemes.

Andie was a magazine writer frustrated by the lightweight “How To” assignments she was expected to produce. Hoping eventually to tackle more meaningful subjects, she agreed to conduct an experiment: date a man and deliberately commit the relationship mistakes that supposedly drive men away, documenting whether she could lose him within 10 days.

Ben, meanwhile, was an advertising executive trying to prove he understood women well enough to win a major diamond account. His wager was the exact opposite of Andie’s mission: he claimed he could make any woman fall in love with him within 10 days.

Neither knew the other was running an experiment.

That contradiction created everything from Andie naming Ben’s anatomy “Princess Sophia” to sabotaging poker night, manufacturing photos of their imaginary future children and nearly destroying the famous love fern.

But underneath the absurdity, Andie and Ben actually began liking each other.

By the movie’s final stretch, their schemes were exposed publicly during the diamond gala. Andie later prepared to leave New York for Washington, D.C., while Ben discovered she had written honestly about what happened between them. His motorcycle chase stopped her taxi and turned what could have been a breakup into the movie’s final reconciliation.

Audiences clearly responded. The film eventually earned roughly $177.6 million worldwide and more than $105 million domestically.

The difficulty for a sequel is that the original trick cannot simply happen again.

Andie cannot plausibly spend another 10 days pretending to be an unbearable girlfriend while Ben secretly makes another romantic bet.

More importantly, dating itself no longer looks like it did in 2003.

The first movie existed in a world of magazine columns, office bets, landline-era misunderstandings and meeting someone in a bar without immediately searching their entire history online.

A modern version would exist alongside dating apps, social media, ghosting, relationship soft-launches, screenshots, read receipts and a completely different media business from the one Andie worked in.

Even Andie’s career presents a question.

In 2003, she wanted to escape formulaic lifestyle journalism and write about subjects that mattered to her. Twenty-three years later, would she still be writing? Running a digital publication? Hosting something? Would Ben still be working in traditional advertising after an era that transformed the entire industry around influencers, algorithms and social platforms?

Those possibilities are still speculation; Paramount has not announced the sequel’s plot. But they illustrate why finding the screenplay matters more than merely convincing two famous actors to return.

Hudson has been saying essentially the same thing for years.

In 2024, she said both she and McConaughey were open to revisiting the movie, but emphasized that the deciding factor would be whether they responded to the script. McConaughey had previously described How to Lose a Guy in 10 Days as a romantic comedy naturally positioned for a follow-up.

Hudson has also imagined very different versions of Andie and Ben’s future.

In a 2020 interview, she pictured them married with children — and joked that they might be miserable by then. By the movie’s 20th anniversary in 2023, her vision sounded warmer: she hoped they were happy, had several children and were still playing the Barry family’s favorite card game with Ben’s parents.

That may contain the sequel’s real opportunity.

The first film asked whether two people could accidentally fall in love while both were lying about why they were dating.

The second could ask something the original never had to confront: whether that relationship survived ordinary life.

Twenty-three years of marriage, children, careers, aging parents, disappointments and compromises would create conflicts that cannot be solved simply by exposing another secret wager.

And if the filmmakers want nostalgia, the original still offers plenty to bring back.

Few images from early-2000s romantic comedies are more recognizable than Hudson descending the staircase in Andie’s backless yellow gown during the diamond gala.

Even that dress has a story.

Costume designer Karen Patch worked around the color of the jewelry Andie would wear, particularly the yellow “Isadora” diamond. Vogue has described the Harry Winston piece as an approximately 84-carat canary-yellow diamond pendant valued at roughly $5 million to $6 million. The gown was created to complement the stone rather than simply having expensive jewelry added afterward.

And the diamond was not an ordinary movie prop.

Hudson has recalled that it was real and that bodyguards were present while it was being used on set.

The dress, the diamond, the love fern, the motorcycle and Ben’s “Frost Yourself” campaign are easy pieces of nostalgia to resurrect.

The harder part is figuring out who Andie and Ben became when the closing credits stopped protecting them.

In 2003, Andie had ten days to make Ben leave.

Twenty-three years later, the harder question may be what happens when two people actually stayed.