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Let me take you back to 1999. No, not to party; to remember the golden age of the Hollywood romโ€‘com. 10 Things I Hate About You. Notting Hill. Runaway Bride. Sheโ€™s All That. It was truly a glorious yearโ€”the pinnacle of the meetโ€‘cute, the makeover montage, the quirky best friend, and the ohโ€‘soโ€‘nearlyโ€‘tragic miscommunication.

It was the year of the Julias: the year Julia Roberts told Hugh Grant, โ€œIโ€™m just a girl, standing in front of a boy, asking him to love her,โ€ and the year a tearful Julia Stiles told Heath Ledger, โ€œI hate the way I donโ€™t hate you. Not even close, not even a little bit, not even at all.โ€ These films were an event. Rather than just shuffling from the kitchen to the sofa, dropping popcorn down our pajamas to the familiar โ€œtu-dumโ€ of Netflix, we actually left the house to watch them. We put on real clothes, sat with other humans, paid actual money. Romโ€‘coms were the reliable engine of the Hollywood box office; from the late โ€™80s to the early โ€™00s, the genre was a dependable hit.

But 20 years on, the story was very different. By 2019, lovelorn white girls had been replaced by men in spandexโ€”the top films included Avengers: Endgame, Spiderโ€‘Man: Far From Home, and Captain Marvel. As studios shifted toward global blockbuster franchises, executives increasingly questioned the value of midโ€‘budget romโ€‘coms. Why finance several $30 million films when a single superhero movie could outperform all of them combined at the worldwide box office?

And perhaps people had grown a little tired of the tropes. The big namesโ€”Sandra Bullock, Meg Ryan, Matthew McConaughey, Hugh Grant, the Juliasโ€”were ready to move on, settle down, age out of the cutesy roles we first met them in. Their knees were getting too bad to run to another airport, stiff after all those damp declarations of love in the rain. Perhaps love had run its course.

Big mistake. Huge. Love never really left. Yes, for a while, the passion burned less brightly than it once did, but the flame was still there. We have always been poised, ready to sneak back and fan it. If the love was truly gone, would we still come crawling back every Christmas, ready to put aside some problematic fat jokes and workplace harassment to rewatch Love Actually for the hundredth time?

The genre was quiet for a whileโ€”it went away, took some time to work on itself. After all, it needed to do some serious thinking about beauty, gender, and consent. But it has been creeping back. Itโ€™s not the same; our relationship with the romโ€‘com has changed, matured. The naive rose-tinted early days are gone. What we are left with is something more battered and fatigued, more complicatedโ€”more real. But we were ready for that. We needed jaded. We are now in the age of Bumble, not boom boxes, after all.

And, sadly, the romโ€‘com event is no more. Slipping quietly onto our home screens in recent years, the genre has shifted from dinnerโ€‘andโ€‘aโ€‘movie date nights to Netflixโ€‘andโ€‘chill. On streaming services, films such as To All the Boys Iโ€™ve Loved Before, Set It Up, The Kissing Booth, and Always Be My Maybe became hits online instead of in theaters; all while romantic dramas in series form began to rework the formula for bingeโ€‘watching. Some of the most talkedโ€‘about shows of 2026 so far have had love at their heartโ€”from the classic Cinderella story in the latest season of Bridgerton to the wellโ€‘trodden enemiesโ€‘toโ€‘lovers arc in the sleeper hit Heated Rivalry. In an era that screams โ€œItโ€™s Complicated,โ€ we are desperate to see happiness on screen.

We have always loved love. We just expected it to grow up a little bitโ€”to be more diverse, more nuanced, and, postโ€‘COVID, to follow us onto our couches. This reading list details some individual films that can trace this journey over the decades. I hope, by the end, you will agree: From the multiplex to the algorithm, there has always been a place for the romโ€‘com.

This Valentineโ€™s weekend, find your favorite film, nostalgic or new, and embrace the genre. Itโ€™s not dead yet.

When Harry Met Sally Makes Adult Weekends Aspirational (Bekah Waalkes, Electric Literature, November 2021)

Weโ€™ll start way back in 1989, with a film that grossed over $93 million at the box office. When Harry Met Sally . . . helped shape the template for the classic friendsโ€‘toโ€‘lovers romโ€‘com, asking whether men and women could ever really be โ€œjust friends.โ€ Bekah Waalkes admits to being fascinated by this dynamic, but even more in awe of Meg Ryan, who she memorably describes as โ€œthe original disheveledโ€‘chic romantic comedy heroine, the patron saint of highโ€‘maintenance white women.โ€ But itโ€™s one particular detail of the film that captivates her most: Harry and Sally hang out on weekends. Their time together isnโ€™t squeezed into rushed weeknights; they take long sunlit walks, they amble around the Met, they help friends move. At a time when Waalkes was struggling to find meaning in her own weekends, Harry and Sally โ€œpainted a picture of a life I wanted . . . wandering around and having witty conversations with my friends.โ€

Everyone can take away something different from a romโ€‘com. For Waalkes, When Harry Met Sally . . . doesnโ€™t stand out for the big gesturesโ€”not the rush to find each other on New Yearโ€™s, nor even the famous fake orgasm scene. She finds comfort in the idea of simply spending time together: the small, ordinary plans that become meaningful just because you share them.

Weekends might be the background for the film, but theyโ€™re also what makes the relationship possible. Sure, When Harry Met Sally wants us to think that a scene at the Met is important because itโ€™s the first time Harry asks Sally out. But if we can look past the plot of the film, weโ€™ll see a relationship that unfolds over weekends. With Harry and Sally, weekends are an opportunity for connection, for catching up. I realized, in my tiny apartment in Budapest, holed up and lonely without the crush of schoolwork, that When Harry Met Sally was just as concerned with how to fill free time as I was. What would be a worthwhile way to spend a Saturday and Sunday was always changing for both Harry and Sally: after all, in the Met, their midday moment is the highlight of Harryโ€™s weekend. But for Sally, itโ€™s merely a quick stop on the way to bigger things. She has a date that nightโ€”and Harry spent their whole afternoon together trying to ask her out. They both leave that afternoon feeling differently.  

While You Were Sleeping as a Balm for Homesickness (Hope Rehak, Bright Wall/ Dark Room, November 2023)

While You Were Sleeping used to be my favorite rom-com, but a recent rewatch left me more squirmy than cozy; it turns out Iโ€™m now a bit less at ease with pretending an unconscious man is your fiancรฉ while his brother hits on you. Still, itโ€™s a โ€™90s classic, with Sandra Bullock in peak America-sweetheart mode.

For Hope Rehak, though, the real star isnโ€™t Bullockโ€”itโ€™s Chicago, Rehak’s home city. Where most romโ€‘coms cast New York as the side character, this one belongs to the wintry Midwest: freezing, gray, and studded with tiny, perfect details. (Thereโ€™s a random 12โ€‘second insert of a paperboy wiping out on the ice, a moment Rehak says every Midwesterner recognizes.) Bullockโ€™s Lucy, described as โ€œan isolated single woman, complete with sad cat and dead parents,โ€ is as stoic about the weather as she is about her lonely-cat life. She doesnโ€™t dream of glamour; just to be loved.

After various shenanigans, Lucy does, of course, find both love and family, content with Chicago because, as Rehak writes, โ€œThe weather isnโ€™t something to be overcome or ignored, itโ€™s something you tolerate, because your family is there.โ€ Rehak offers a loving homage to a romโ€‘com classic, a sharp commentary on class, and a moving portrait of what it means to be a homesick Chicagoan.

While You Were Sleeping (1995) is the one movie that captures that Chicago, the sensibilities we have towards civic pride and community care. It shows some authentic corners of downtown and the northwest sideโ€”thereโ€™s Lucyโ€™s early 20th century eight-flat, the Callaghansโ€™ suburban house, and Peterโ€™s Lake Point Tower high-riseโ€”and it captures the same off-beat humor and hard-won earnestness of the people. Consider the romantic comedy genre as a form of science fiction: All movies require a constructed world, and all rom-com settings require a situation hermetically sealed off from the rest of human suffering in order to elevate the small injuries, emotional highs, and petty lows of dating, sex, and marriage to the height of importance. Within that framework, limited though it can be, While You Were Sleeping nails it. 

โ€™Tis the Season to Kill the Dead-Mom Holiday Movie Trope (Cat Modlin-Jackson, Longreads, December 2023)

As we edge toward the early 2000s, weโ€™re leaving the era of peak rom-com. That is, except for at Christmasโ€”rom-com cheat season. In this piece, Cat Modlin-Jackson looks at some of the holiday heavy hitters: Love Actually (2003), The Holiday (2006), and Falling for Christmas (2022). She has a serious bone to pick with them, though: their casual use of the โ€œdead mom trope.โ€

In Falling for Christmas, for instance, widower Jake Russell is struggling to raise his daughter, Avy, until, as Modlin-Jackson writes, โ€œa concussed heiress named Sierra (Lindsay Lohan) reignites Jakeโ€™s loins.โ€ Naturally, Sierra has also lost her mother, giving her something to bond over with Avy. But what happens when this supposedly heartwarming plot device hits too close to home?

Reflecting on the death of her sister-in-law, Modlin-Jackson lays out the reality of navigating Christmas after losing someone you loveโ€”and doing it without a hunky Jude Law stand-in. She treads a difficult line with skill, managing to be both very funny and genuinely furious. The laughs are real, but so are the painfully sharp observations on grief.

Christmas and death have a weird bond. To act like the latter doesnโ€™t exist amidst the former would be ridiculous. Between Charles Dickensโ€™ merry band of ghosts and a month full of birthday parties for a guy who dies twice after a miraculous birth, Christmastime is one big existential crisis. And sure, a movie can portray loss and grief in a way that the left-behind can actually connect with, and maybeโ€”just maybeโ€”derive a little lightness from. But for that to work, the plot would have to focus on what already exists. To get really corny about it, the magic would have to come from within. That kind of magic is a slow burn; itโ€™s moving forward rather than moving on, whether thatโ€™s a daughter who gets by with a little help from her friends or a widower who gets closer to his sister as they help the kids navigate the world without their mom. Itโ€™s learning how to live a new life thatโ€™s always going to be laced with death.

How the โ€˜To All the Boysโ€™ Franchise Revitalized the Rom-Com for the Streaming Age (Ellise Shafer, Variety, March 2021)

Aside from the yuletide fare, by the 2010s, we were on something of a romโ€‘com hiatusโ€”until the genre reemerged with a bang in its new home: streaming platforms. A few titles led the way, but the first major streaming romโ€‘com phenomenon was To All the Boys Iโ€™ve Loved Before (2018). Netflix claimed the first film (there are three in total) as one of its mostโ€‘viewed originals ever, and the franchise built a fandom of millions, including over two million followers on its official Instagram account.

An honorable mention needs to go to The Summer I Turned Pretty, another Jenny Han adaptation, that took the world (and TikTok) by storm last summer. Fans built a huge community around personal reflections on the show. And yes, I, too, found myself strangely obsessed by a teenage love triangleโ€”between the beautiful Belly and two brothers (yes, brothers). While technically a series, not a rom-com, it still shows the massive following the romance genre can create. To find out more, read Sara Radinโ€™s fascinating article for Elle, โ€œWhy Almost Every Woman You Know Is Obsessed Withย The Summer I Turned Pretty.โ€ #TeamConrad.ย 

As Ellise Shafer writes, its success lies in how it updates the romโ€‘com formula into โ€œa more inclusive version of the story, with an Asian American girl at its center, and more fully realized supporting characters around her.โ€ Shafer talks to the people behind the films, including Jenny Han, author of the books, whoโ€”with Hollywood unwilling to accept an Asian American leadโ€”took the project to Awesomeness Films. The then head of their film division, Matt Kaplan, โ€œa lifelong lover of romโ€‘coms like those of director John Hughes,โ€ saw an opportunity to revitalize the genre into something both modern and commercial. Shafer quietly unpacks how a young adult book trilogy became the blueprint for a new era of streaming romโ€‘coms.

โ€œWe were kind of ahead of the movement and I think thatโ€™s why we were attracted to the material. The worldโ€™s changing, you know?โ€ Kaplan says. โ€œHaving a young, female, empowered lead character who is Asian American and has a global connection, I think thatโ€™s why youโ€™re seeing that moment happen. People sit down to watch a movie or a show because they want to connect to whatever theyโ€™re going through in the story theyโ€™re watching. Ultimately, telling stories that are modern is what will make rom-coms work.โ€

โ€˜Tears Were Running Down My Faceโ€™: Why Bridget Jones 4 is the Most Moving Rom-com of Modern Times (Barbara Speed, Catherine Shoard, Lucy Knight, Hollie Richardson, Emmy Griffiths, Anne Billson, Samuel James, Kira Cochrane, Gwilym Mumford, and Laura Snapes; The Guardian, February 2025)

We couldnโ€™t forget Bridget Jones. The chaotic rom-com heroine has been with us for nearly 25 years and neatly charts the genreโ€™s evolution. The early films were bigโ€‘screen box office events; the latest installment went straight to streaming in the US. The first movie, released in 2001, is an uncomfortable watch now: Bridget is repeatedly referred to as fat (at 130 pounds), and workplace misogyny is played for laughs. Fastโ€‘forward to 2025โ€™s Bridget Jones: Mad About the Boyโ€”the subject of this Guardian pieceโ€”and we have an altogether more thoughtful affair. It confronts middle age, grief, and single motherhood headโ€‘on (and, admittedly, the joys of being a cougar).

Here, 10 Guardian writers offer their impressions of the new film, and I was moved by every one. Hollie Richardson describes being โ€œfloored by the memories of a relationship Iโ€™ve been rooting for since I was barely a teenager.โ€ Gwilym Mumford reflects on Hugh Grant: the onceโ€‘stammering โ€™90s heartthrob who revels in portraying a fullโ€‘blown scoundrel in the Bridget franchise, โ€œarmed and ready at all times with a smutty, absurdist zinger whenever things are getting too introspective.โ€ Laura Snapes admires the depiction of Bridgetโ€™s old friend groupโ€”played by the same cast for 24 yearsโ€”noting how โ€œoldest, closest friends keep the essence of each other alive, that profound depth of mutual understanding allowing us still to be just the way we are.โ€ Emmy Griffiths zeroes in on the filmโ€™s main subject: grief, writing that she spent most of the film sobbing because it โ€œcaptures the crushing sadness of losing someone essential, but also [offers] gentle guidance on how to move on.โ€ Unlike all those Christmas rom-coms, this is a film that handles loss realistically, unflinchingly.

I first met Bridget in the early 2000s, when I lived in London and read the books, seeing echoes of myself in her shambolic dating life and heavy-drinking friend group. I last spent time with her this past summer, rewatching all the films with my mum while she was battling cancer. Sick as she was, my mum still managed to smile at Bridgetโ€™s antics, still called Mark Darcy โ€œdishy,โ€ still tutted at what โ€œa cadโ€ Daniel Cleaver was. Bridgetโ€™s world has aged and developed over the years, and so has mine, so has all of ours. This filmโ€”a beautiful example of the new age of the rom-comโ€”reminds us that even as life gets harder and more complex, thereโ€™s still room for laughter. And for love.

Laura Snapes:

The first bit of BJ4 that got me was Bridgetโ€™s lovely dad, in his dying days, telling his widowed daughter that it wasnโ€™t enough to survive, she also had to live. Much of Mad About the Boy dwells on her fears around how to keep the late Mark Darcyโ€™s memory alive for their children, and as others have said, the filmโ€™s most tear-jerking moments are those explicitly about preserving Mark in song, in celibacy and by shunning awful so-called memorial dinners with pitying โ€œfriendsโ€ (the Cosmo and Woney!) for a much more fitting ad hoc pub wake with her gang, over blue cocktails (hopefully made from authentic string-based colouring).

Lucy Knight: 

By the time Bridgetโ€™s son Billy performs the song his father used to sing to him at his school concert, tears were running down my face. An earnest, grieving child singing angelically is obviously a moment designed to make us bleary-eyed, but this doesnโ€™t feel gratuitous โ€“ it serves the plot, in that by Billyโ€™s teacher (Chiwetel Ejiofor) arranging this performance, he reveals his kindness to Bridget, cementing himself as a worthy suitor. It speaks to how we all grieve differently, and how amazing it feels when someone takes the time to understand what we really need.


Copyeditor: Krista Stevens