The Enduring Allure of '90s Romance

From JFK Jr. and Carolyn Bessette-Kennedy to meet-cutes on the big screen, the nostalgia for vintage love stories remains strong.

Mar. 27, 2026 at 2:20am

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Writer Emma Firth explores the ongoing fascination with '90s-era romance, from the real-life relationship of JFK Jr. and Carolyn Bessette-Kennedy to the enduring appeal of classic romantic comedies like "Notting Hill" and "You've Got Mail." Firth argues that the slower, more analog courtship rituals of the pre-digital age hold a special charm in a world increasingly dominated by online dating and social media.

Why it matters

The popularity of '90s-set love stories reflects a broader yearning for a bygone era of romance, when courtship was more about in-person connection and mystery rather than curated online profiles. This nostalgia speaks to a desire to reconnect with a more analog, present-focused approach to relationships.

The details

Firth delves into the appeal of shows like "Love Story" that dramatize the relationship between JFK Jr. and Carolyn Bessette-Kennedy, as well as the enduring popularity of '90s romantic comedies. She interviews experts like poet Matt Starr who discuss how these vintage love stories capture a sense of being "present" and engaged in the real world, rather than distracted by technology. Firth also highlights real-life couples who share their own '90s-era meet-cute stories on social media, further fueling the nostalgia.

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The players

Emma Firth

A writer and romantic who explores the enduring appeal of '90s-era love stories.

Matt Starr

A poet and co-founder of Dream Baby Press who discusses the charm of vintage romance on-screen.

Pamela Marshall

A clinical aesthetician who recalls the slower, more analog dating rituals of the late 1980s.

John F. Kennedy Jr.

The son of former U.S. President John F. Kennedy, whose relationship with Carolyn Bessette-Kennedy has become a subject of renewed fascination.

Carolyn Bessette-Kennedy

The wife of John F. Kennedy Jr., known for her iconic '90s fashion and the high-profile nature of their relationship.

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What they’re saying

“If there's any kind of magic in this world, it must be in the attempt of understanding someone, sharing something. I know, it's almost impossible to succeed but who cares really? The answer must be in the attempt.”

— Céline

“For most of us, we met people through friends, dinner parties, bars or clubs... The dating was slower, and there wasn't the mobile phone to text in-between. I loved the anticipatory wait for the next date—we'd get excited because you'd not seen him or her in a while, and there was just so much to talk about, to catch up on. A lot was still a mystery because there just wasn't the constant interaction in-between dates.”

— Pamela Marshall, Clinical Aesthetician

“Handwritten anything is so special. A note, a letter. Whatever. Ask someone out with a handwritten note. Go on walks. Go see art. Go to a museum. Don't go to bars. Be brave.”

— Matt Starr, Poet, Co-founder of Dream Baby Press

What’s next

As the '90s continue to be a source of nostalgia, it's likely that more TV shows, films, and social media trends celebrating the romance of that era will emerge in the coming years.

The takeaway

The enduring appeal of '90s-era love stories reflects a broader longing for a more analog, present-focused approach to relationships. In an increasingly digital world, the slower courtship rituals and in-person connection of the pre-internet age hold a special charm, fueling our collective fascination with vintage romance.