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A 90’s Rom-Com Inspired NYC Engagement Session | Elizabeth + Jared

Some engagement sessions are built around a location.

Others are built around an aesthetic.

Elizabeth and Jared’s session was built around a feeling.

The kind of feeling that makes you want to rewatch your favorite 90’s romantic comedy for the hundredth time. The kind where New York City isn’t simply the backdrop—it becomes part of the story. The neighborhood pizza shop on the corner. The tree-lined streets glowing in the late afternoon sun. Brownstone stoops, bustling crosswalks, little cafés, and quiet moments tucked inside one of the busiest cities in the world.

It felt nostalgic.

Playful.

And somehow familiar, even if you’ve never met them before.

As a New York City engagement photographer, these are the sessions I love most—not because they’re perfectly styled, but because they allow couples to create photographs that feel like memories instead of poses.

Their Story Started with an Elevator Conversation

Love stories rarely begin the way we expect them to.

Elizabeth and Jared first crossed paths at an entrepreneurship event in New York City. They had both arrived late, stepped into the same elevator, and found themselves in one of those wonderfully unexpected moments that can quietly change everything.

Jared broke the silence with a simple observation:

“Nobody ever talks in elevators.”

That one sentence turned into a conversation that lasted nearly half an hour. Although they went their separate ways afterward, the connection stayed with them. A few months later, they matched on Hinge, and this time, the conversation didn’t end when the elevator doors opened.

Looking back, it’s hard not to smile at how ordinary moments often become extraordinary in hindsight. Their story didn’t begin with fireworks or grand gestures. It began with curiosity, a little courage, and someone deciding to say hello.

Falling in Love with New York—and Each Other

One of my favorite questions to ask couples is when they realized their relationship had become something more.

For Elizabeth and Jared, that moment came after spending a weekend together in the city. Sitting in Riverside Park overlooking the Hudson River, they found themselves talking about life, the future, and everything in between. It wasn’t a dramatic declaration. It was something quieter—the realization that they simply didn’t want the weekend to end.

That answer perfectly captures the feeling of this engagement session.

Rather than chasing iconic landmarks simply because they’re famous, we photographed the version of New York City that belonged to them. The neighborhoods they wandered through. The sidewalks they laughed on. The everyday corners that quietly became part of their relationship.

That’s what makes a city feel like home.

A Session Inspired by the Movies We Grew Up Loving

When planning an engagement session, I always encourage couples to think beyond locations.

Instead, I ask them to think about how they want their photographs to feel.

Elizabeth and Jared wanted something nostalgic, cinematic, and unmistakably New York. Together, we leaned into the effortless charm of classic 90’s romantic comedies—the kind of films where the city becomes another character in the story.

As we wandered through Manhattan, every stop felt like a different scene unfolding.

Sharing a slice of pizza at a neighborhood restaurant.

Laughing beneath the trees in golden-hour light.

Walking hand in hand across busy intersections without worrying who was watching.

Sitting together on historic brownstone steps.

Even the black-and-white photographs carried the timeless quality of an old film still, allowing the emotion to take center stage.

Nothing about the session felt overly styled or manufactured.

Instead, it felt wonderfully lived in.

As though these photographs had been pulled from memories rather than created during a photoshoot.

Why New York City Is One of My Favorite Places for Engagement Sessions

There’s a reason so many love stories have been set in New York City.

The city offers an endless variety of textures and emotions. One moment you’re surrounded by towering buildings and busy sidewalks. The next, you’ve slipped into a quiet park where the sounds of the city fade into birdsong and rustling leaves.

That contrast creates something incredibly special for engagement photography.

Every neighborhood offers its own personality. Every block tells a different story. And because no two couples experience New York in exactly the same way, no two engagement sessions ever feel alike.

For Elizabeth and Jared, the city wasn’t simply where we took photographs.

It was woven into the story we were telling.

Their session became less about documenting landmarks and more about preserving what it feels like to fall in love in New York.

A Proposal That Came Full Circle

One of my favorite parts of Elizabeth and Jared’s story is that their engagement wasn’t simply a surprise—it was deeply intentional.

Jared brought Elizabeth back to the Made Hotel rooftop, the very place where their story first began. He surprised her with flowers, proposed overlooking the city, and then planned an entire weekend celebrating with the people they love most, ending with a surprise engagement party.

There’s something incredibly meaningful about returning to where it all started.

Rather than searching for somewhere extravagant, he chose a place that already held significance. It was a reminder that the most memorable moments aren’t always created somewhere new—they’re often found by revisiting the places that quietly changed your life.

Knowing that story before photographing their engagement session made every location throughout Manhattan feel even more meaningful. This wasn’t simply a beautiful afternoon in New York City. It was another chapter in a love story the city had been witnessing all along.

The Best Engagement Sessions Feel Like a Date

One of the biggest misconceptions about engagement sessions is that they have to revolve around posing.

I couldn’t disagree more.

The most memorable engagement photos rarely happen because I told a couple exactly where to stand. They happen because I give them something to experience together.

For Elizabeth and Jared, that meant slowing down enough to enjoy the city they love.

Stopping for pizza.

Walking through familiar streets.

Laughing as they crossed intersections.

Sitting together on brownstone stoops.

Sharing quiet moments beneath the trees in Central Park.

None of those moments felt staged because they weren’t trying to perform for the camera. They were simply spending an evening together while I documented what naturally unfolded.

That’s always my goal.

To create photographs that feel like memories instead of directions.

Why New York City Is the Perfect Place to Tell a Love Story

There’s a reason New York has inspired generations of filmmakers, writers, and artists.

It’s a city built on stories.

Every neighborhood carries its own rhythm. Every block offers another possibility. The energy constantly shifts depending on where you are, making it one of the most versatile places in the world for engagement photography.

Within just a few hours, couples can move from tree-lined parks to historic brownstones, bustling sidewalks to intimate neighborhood restaurants, elegant architecture to quiet hidden corners.

For photographers, that variety is endlessly inspiring.

For couples, it means your engagement session never has to feel like anyone else’s.

Elizabeth and Jared embraced that beautifully.

Rather than chasing iconic tourist photos, they leaned into the version of New York that felt most authentic to them. The result was a gallery that feels timeless because it’s rooted in experience rather than trends.

Years from now, these photographs won’t simply remind them what New York looked like.

They’ll remember exactly how it felt to walk those streets together before becoming husband and wife.

Why I Love Photographing Editorial Engagement Sessions

One of my favorite things about engagement sessions is that they’re often the first opportunity couples have to simply slow down together.

Wedding days are beautifully full.

Timelines move quickly.

Family and friends surround you from morning until night.

An engagement session is different.

There’s space to wander.

To laugh.

To stop for a slice of pizza.

To take the long way through the park.

To sit quietly without feeling rushed.

Those slower moments allow personalities to shine through in a way that wedding days sometimes can’t.

My approach has never been about creating perfectly posed images.

It’s about documenting connection.

The subtle glance across the table.

The way someone instinctively reaches for the other’s hand.

The laughter that happens after a joke no one else hears.

Those are the photographs that continue to matter long after the wedding has passed.

Planning Your Own NYC Engagement Session?

If you’re planning a New York City engagement session, my biggest piece of advice is this:

Choose locations that mean something to you.

Maybe it’s the neighborhood where you met.

Your favorite coffee shop.

The park where you spend Sunday mornings.

The restaurant where you celebrated your first anniversary.

Or maybe it’s simply the streets you walk together every day.

The most beautiful engagement sessions aren’t defined by famous landmarks—they’re defined by personal stories.

Whether you’re envisioning an editorial session through Manhattan, a quiet morning in Central Park, or a nostalgic concept inspired by your favorite films, I’d love to help create photographs that feel like you.

Because years from now, I don’t want you to remember where I asked you to stand.

I want you to remember how it felt to fall in love. Reach us out here.