Intro for August 25, 2026

Dear Gossips,

No list of rom-coms from the last 25 years would be complete without How To Lose a Guy in 10 Days. It’s a classic, complete with several classic rom-com elements: it’s a workplace story, there’s a bet on the line, a fake relationship, and of course a dress so memorable it’s cinematic history.

All you have to do is start your google search with “yellow dress” and the rest will be filled in for you.

@peacock The dress that has generations in a chokehold. #HowToLoseAGuyIn10Days is streaming on Peacock. #KateHudson #MatthewMcConaughey #BebeNeuwirth #KathrynHahn ♬ Peacock_HowToLoseAGuyIn10Days_AndiesDress - Peacock

Like so many rom-coms from its time, How To Lose a Guy in 10 Days was not well received by critics when it came out. It was February 2003, way before streaming, when releasing films in that month typically meant low expectations for box office performance. But it was a week before Valentine’s Day, and people were in the mood. The movie was a hit, grossing almost $180 million on a $50 million budget and continued to bring in money after its theatrical run with at-home viewing. Matthew McConaughey recently said that he’s still getting paid from it, that’s how popular it continues to be as new audiences discover it. So it’s definitely not just those of us who were around and old enough at the time who remember it.

Vanity Fair published an oral history about How To Lose a Guy in 10 Days three years ago to celebrate its 20^th anniversary and, fun fact, it was originally supposed to be Gwyneth Paltrow playing Andie Anderson but she had to drop out for scheduling reasons and that’s when Kate Hudson stepped in.

The movie turns 25 in 2028, will they be able to get the sequel done in time? Variety reported today that the project is in development with Kate Hudson on board as one of the producers. But it’s super early – they’re still working out the story and looking for a screenwriter so there’s really not much to say beyond that. Like it doesn’t even sound like Matthew McConaughey is officially involved yet. Not that he wouldn’t be once they figure sh-t out, but the point is, we really don’t have much to go on right now and it’s way more complicated than bringing together the two leads.

For starters, so many rom-coms, most rom-coms, are about the beginning: two people meet, they are attracted to each other, there’s an obstacle that has to be confronted, but not before a breakup, which leads to personal growth beyond the romance, and then a late third realisation resulting in a chase, either on foot or a scooter or getting a last minute flight, and then a confession, sometimes in public.

But we rarely find out what happens after. When a relationship has to stabilise, and truly develop after the initial intensity. This is the “boring” phase – critical in real life to the longevity of a couple but not necessarily cinematic. And that’s also why, usually, at least among the most well-known rom-coms, people are never over 40.

It’ll be interesting then to see how they get back into Andie Anderson and Benjamin Barry’s story. Not just where their relationship is concerned but also their careers since, as noted, this was a workplace romance – and all these years later, their respective workplaces have changed so much. Advertising executives aren’t thinking about billboards anymore, they’re working on viral TikToks. And magazine writers? That’s a bitter LOL. Andie was a staff writer at a women’s magazine who had weeks to work on a story. Kate Hudson said last year that a lot of women have told her that they became journalists because of that movie.

@voguemagazine Andie Anderson walked so we could run. Tap the link in bio to watch #KateHudson and #HughJackson talk #SongSungBlue and more on Vogue’s #TheRunThrough ♬ original sound - Vogue

Andie Anderson and Andy Sachs, who came after her in The Devil Wears Prada, wanted to write about more than just “How To” date a guy or lose a guy or wear low-rise jeans. And we found out recently in Prada 2 just how volatile, even precarious, it can be to maintain a career as a writer – for a newspaper, for a magazine, for an online publication, for anyone writing anywhere. That’s what I appreciated about The Devil Wears Prada 2, even though it was triggering: it was a love letter to legacy media. And I’m curious to see whether or not the sequel to How to Lose a Guy in 10 Days even goes there…

On top of the main dating story and the original movie’s meditation on dating behaviour. These days, the wrong punctuation, an accidental period at the end of a seemingly innocuous sentence, can get you ghosted during an initial text exchange on a dating app. Periods, apparently, are “aggressive”.

Still, the enduring appeal of How To Lose a Guy in 10 Days, especially right now, with 90s and 2000s pop culture experiencing such a resurgence, is undeniable. I get why this project was pitched. But just as it is with rom-coms, the pitch (or the initial spark) is the easy part, getting the rest of it over the line is the challenge.

Yours in gossip,

Lainey