Letters from Esther #68: Daters Are the Pioneers of Modern Love

Shall We Begin?

Meet Ally, Louis, and Douglas: three strangers, three different life stages, all actively dating and in search of love, pleasure, and passion. I recently had a conversation with all three of them—a blind date, if you will—for my podcast, Where Should We Begin? They each brought their own questions, quiet fears, and hopes they weren’t even sure they were allowed to name.

What unfolded was more vulnerable than a conversation about dating apps and swiping behavior. It was a reflection on longing, loneliness, doubt, curiosity, and culture. They are all searching for real connection in a world that doesn’t feel designed for it. Welcome to modern dating.

THE DATERS

Louis, a gay man in his late twenties, was born in Cameroon and came out after moving to the U.S. He’s gregarious and open-hearted—someone who genuinely enjoys the experience of meeting new people. But he’s noticed a pattern: feelings rise quickly and then disappear just as fast. “It always goes from really high to nothing,” he says. And yet, he keeps showing up. “I still go in with a big smile.”

Douglas, who moved from South Korea to Los Angeles just over a year ago, is dating with serious intention for the first time. He adopted the name “Douglas” because his Korean name is hard for many to pronounce—one of many subtle ways he’s had to translate himself to be understood. He’s thoughtful, sincere, and emotionally observant. But when it comes to dating, he finds it hard to feel that elusive spark. “Sometimes I perform curiosity,” he admits. “I wish I didn’t have to.” Underneath is a quiet ache: Why is it so hard to feel something real?

Ally is a 47-year-old straight woman and divorced mother of two who grew up in Saudi Arabia and now lives outside Boston. After a long marriage, she’s re-entered the dating world with both curiosity and caution. She calls the process tedious, something that competes with the few hours she has to herself after work and parenting. “When I go on a date, it’s taking time away from people I already love, or from being alone, which I actually enjoy.” Still, she holds onto hope.

DON'T BE SO QUICK TO JUDGE

Let’s be clear: these aren’t stories of dysfunction. They’re stories of resilience. And improvisation. Trying and trying again. All three are doing something that wasn’t modeled for any of us: building intimacy outside of kinship networks, without reliable introductions from friends, without shared context—because modern dating takes place in a world that doesn’t look the same as it did when our parents and ancestors were courting. They didn’t know the experience of sitting at home alone, face aglow from a phone screen, looking for love.

Modern daters are pioneers of new rituals and new rules. They must find new answers for age-old questions that have been transformed by technology, globalization, consumerism, and individualism. How will I choose? And will they choose me? How much is too much to share? What happens if I get my heart broken again?

EMOTIONAL MULTITASKING

Dating today is an act of emotional multitasking. It asks us to hold hope and disappointment in the same hand. It asks us to stay open to intimacy while guarding against burnout. It asks us to reveal ourselves just enough to spark interest—but not so much that we seem too eager.

What stayed with me most after our conversation was what didn’t come up: We didn’t talk much about love. Or sex. Or desire. We talked about time. Logistics. Ambivalence. Effort. Not because these three people don’t want love—but because they’ve grown used to organizing their romantic lives around systems that reward patience and performance over presence. And yet, in the middle of all that, there were glimmers.

• When Louis spoke about his joy in simply meeting people.
  
• When Douglas described a second date at a climbing gym, planned with care.
  
• When Ally talked about how she can sense real connection—not through words, but through the way someone leans in, or lingers, or asks a real question.

Each of them is reaching for something honest. Not just to be liked. Not just to match. But to be met.​

Click here to listen to this episode on Apple Podcasts.

This episode—titled "Terms & Conditions May Apply"— won’t give you dating rules. But it might give you something better: permission—to date at your own pace; to take breaks when your spirit needs rest; to try new things; and above all, to approach dating with curiosity.

Because when connection starts to feel like a transaction, it’s curiosity—the kind that invites and listens and stays—that brings us back to the part of dating that has remained the same throughout time: to meet and to be met, to see what unfolds.

Know someone who’s dating in the deep end? Consider sharing this letter with them now.

Let’s Turn the Lens on You

Every month in this space, we aim to offer not only reflection, but practical exercises you can bring into your relationships, conversations, or next encounter. This month, we’re excited to share something new.

We’ve partnered with the dating app Hinge to co-create a new collection of profile Prompts called “Your World.” These ten Prompts are designed to help daters share more of who they are—by sparking curiosity, inviting storytelling, and breaking free from familiar scripts. The goal is to help online conversations flow more naturally into meaningful in-person connection. Here’s a small sample of what’s now live on the app:

• In my friend group, I’m the one who . . .
• An award my family would give me . . .
• Where I go when I want to feel a little more like myself . . .

Even if you’re not dating, try answering one of these with a friend or partner. Sometimes the right question is all it takes to turn a moment into a story—and a story into something more.

More from Esther

EROTIC INTELLIGENCE: CULTIVATING DESIRE AND ALIVENESS IN YOUR RELATIONSHIPS | reserve your spot

On October 8–13, 2025, amidst the wonders of Paros, Greece, my expert guest facilitators and I will share fresh perspectives and actionable tools to help you go deeper into the work, expand your erotic intelligence, and experience new erotic breakthroughs—with or without a partner.

TRANSFORM YOUR WORK CULTURE | learn more

I believe that the quality of our relationships at work determines the quality of our work. From my new card game to my class on Masterclass to my limited podcast series How’s Work?, my suite of workplace offerings are designed to help business owners, managers, and team leaders elevate workplace connection and improve team dynamics.

SESSIONS LIVE 2025: MATING IN THE METACRISIS | watch the replay

The live event may be over, but you can still be part of this transformative experience. Register today to get on-demand access and discover:

• A complete archive of recordings
• Exclusive discounts from event partners, plus 10% off my books, courses, and card game
• Additional resources to go even deeper
  
• Unique networking opportunities

You’ll find all this and more inside the Sessions Live app—but only for a limited time.

Conversation Starters

A compendium of highly recommended sources of inspiration and information

TO READ:‍

• The Dry Season by Melissa Febos. With intensity and precision, Febos writes through a year without sex—and emerges with revelations about intimacy, addiction, power, and self-respect. The Dry Season is not a memoir of lack, but of radical clarity.
• Living Real: Redefining Success, Presence, and Happiness by Camille Preston Ph.D.This book is an invitation to high-performers to exit autopilot and reconnect with what truly matters. With unflinching honesty and practical tools, Preston guides readers to reclaim the parts of themselves they’ve sidelined in the pursuit of external success—and to live and lead with greater presence, authenticity, and meaning.
• Raising AI: An Essential Guide to Parenting Our Future by De Kai. This new book offers a powerful reframe: A.I. bots are neither gods nor slaves; they’re imitative, neuroatypical, attention-seeking children who want your approval, and have grown into feral tweens who are humanity’s most giant influencers . . . So, as De Kai asks, how’s your parenting?