Drew's New York City Rooftop Proposal

Rain or Shine, the proposal will go on.

Drew planned the perfect proposal high above midtown Manhattan with a direct and unobstructed view of the Empire State Building. However, mother nature had other plans, as morning showers passed through leaving New York City with fog, which partially blocked the Empire State Building. As Drew proposed, the clouds cleared and slowly the skyline revealed itself.

The Proposal Plan: Drew surprised Sophia at the Midtown Loft and Terrace, where she was supposed to be “meeting friends for brunch”.

Photographing a New York City rooftop proposal is a unique experience

Proposing in New York City is about you, your story, and the now. In my proposal photos I always capture the location, as it’s a part of your proposal story. What makes a rooftop proposal so unique is its ability to capture the NYC skyline with its iconic buildings and unobstructed views. The Midtown Loft and Terrace offers an amazing view of the Empire State Building right behind you.

Jonathan Heisler Photography is comprised of New York City photographers specializing in photographing private NYC proposals, as well as engagement sessions and weddings.

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Neil's Rockefeller Christmas Tree Surprise Proposal

I tell client’s “It’s straight out of a movie, but it’s real life” when helping plan their Rockefeller Christmas tree proposal. While proposing at the Christmas tree around Christmas is chaotic, jam packed with tourists, and somewhat risky from a photography standpoint (people walking in front of you), it sure does make awesome and memorable photos. If you’re willing to have people in your photos in order to capture this unique New York City spot, then let’s go for it!

Christmas in New york, and an engagement!

On today’s session, Neil proposed to Ashley on their long weekend trip to New York City. This was Neil’s first time to NYC, and he found both the crowds and the world famous Rockefeller Christmas Tree to be very impressive.

We started our holiday proposal session at Rockefeller Center and then moved to the shops at Bryant Park for a post-proposal posed mini-session.

It worked out very well photographing Neil and Ashley’s proposal near the Rockefeller Christmas tree just a few blocks North of Bryant Park. After the proposal and several posed photos we moved downtown to Bryant Park. When photographing I took full advantage of all the twinkly lights and making sure to capture the Empire State Building in a few of their photos. Great photos have context.

Jonathan Heisler Photography is comprised of New York City photographers specializing in photographing private NYC proposals, as well as engagement sessions and weddings

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Spencer's NYC Proposal at The Edge

The Proposal Plan: Spencer proposed to Hayden on their trip to New York City to kick off the holiday season! We chose The Edge at Hudson Yards for its unobstructed views of the NYC skyline. The skyline would add context to their moment. Every time I photograph at The Edge, I love it more and more.

Hayden and Spencer arrived at the top of The Edge right on time! Upon seeing them, Spencer and I made eye contact. They walked over and Spencer asked me, “A stranger?”, if I could take a photo of them with his iPhone.

I took several photos with Spencer’s iPhone, and I offered a few instructions on how to pose. Then, Spencer turned to Hayden and started to tell her about all of the reasons he loved her. Spencer dropped to one knee and popped the question. Hayden was so shocked, full of emotion, and simply ecstatic!

Proposing at The Edge, NYC Takes Some Planning

You’ll have to buy tickets to visit The Edge at Hudson Yards, and so will your photographer. Many people ask when is the best time to propose at The Edge, and the best answer is mornings or afternoons, just not mid-day. The lighting is so good at The Edge, as the light reflects off the building onto the viewing deck.

To propose at The Edge and have your moment photographed by a professional proposal photographer, book your tickets, and have your NYC proposal photographer book his/her tickets before you. That way, they are up top before you. I have several recommendations on where up top you should propose and where, but I’ll tell you about that later! Using my experience as a professional NYC Proposal Photographer really pays off when it comes to photographing proposals at The Edge, or anywhere in New York City.

Jonathan Heisler Photography is comprised of Professional New York City photographers specializing in photographing private NYC proposals, as well as engagement sessions and weddings.

LEARN MORE ABOUT HIRING A PROPOSAL PHOTOGRAPHER IN NYC

Headshots of a Professional Photographer

I told myself “no pressure” when photographing headshots of Northwell Health’s official photographer, Lee Weissman. I’ve known Lee for several years now, going back to my days as a university photographer for Hofstra University. In addition to his healthcare work, Lee also photographs sports for Newsday and several other outlets. He’s a jack of all trades.

Proposing In Long Island City's Gantry Plaza | Pierre and Allyson

With NYC skyline views, waterfront piers, and fewer late-night crowds, Gantry Plaza State Park is a strong choice for proposals at night. Pierre chose this location because it balances iconic city elements—Empire State Building, Midtown lights—with a quieter, more private atmosphere than many Manhattan locations.

The Proposal Story

Pierre and Allyson arrived at Gantry Plaza in the evening, after sunset. The city lights were on, the skyline visible, and the piers slightly less crowded. Pierre led Allyson to one of the waterfront piers that frame the skyline with the East River in front. At that vantage point, he proposed.

Photographs include wide views of the skyline, medium shots closer to frame their expressions, and closer portraits to capture emotion. Because lighting changed quickly (serving both ambient light and city lights), multiple angles were used to ensure both the couple and the background were well-exposed.

Why Gantry Plaza State Park Works Well for Night Proposals

• City skyline visibility — landmarks like the Empire State Building and Midtown lights are clearly visible, making for visually striking backgrounds.

• Waterfront reflections — at night, the calm water and lights reflect well, adding depth and visual interest.

• Less crowded at night — fewer people on the piers after dark allow more flexibility with framing and less pressure from bystanders.

• Multiple vantage points — piers, walkways, and gantries offer varied compositions (wide skyline shots, close intimacy) without needing to move far.

Tips for Planning a Night Proposal at Gantry Plaza

• Arrive 30-60 minutes before sunset to scout lighting, shadows, and reflection opportunities.

• Use locations that allow you to see both skyline lights and water reflections. Piers generally work well.

• Dress with layers—nights by the river can be chilly. Accessories like coats, scarves help both comfort and visual layering.

• Bring lighting considerations: city lights, existing lampposts etc. A photographer familiar with low light will help avoid over/ underexposure.

• Choose angles that balance light from the skyline with ambient light so the couple is properly lit without losing the city glow.

Jonathan Heisler Photography is comprised of New York City photographers specializing in photographing private NYC proposals, as well as engagement sessions and weddings.

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Planning and Photographing Alexanders Central Park Proposal

How to plan your secret proposal: A little help from your friends.

Alex enlisted his friend John and his wife to organize and deliver “the supplies” to the exact spot he’d propose in Central Park; hot chocolate, marshmallows, whipped cream, champagne, a dozen roses.

How Alex Proposed: Alex and Casey would walk through Central Park from their Upper West Side apartment to the Upper East Side to meet friends for lunch. This had Casey looking nice!

Alex and Casey’s friends helped bring the hot cocoa supplies in a neatly organized picnic basket. The basket marked the spot where Alex would propose. Later, they regrouped with the newly engaged couple for a quick in person “congrats!” and a group photo.

Finding a private place to photograph a secret proposal in Central Park takes some thinking. Having a professional proposal photographer help you is a huge load off of your shoulders.

Photographing proposals in Central Park is such a contrast from the more typical New York City hustle and bustle proposals with New York City as the background. Today’s hidden spot is in the northern part of Central Park near the reservoir. I love photographing proposals here because the light filters through the trees creating warm even light. This spot provides some privacy between you and tourists in the park, and offers several different vantage points for post-proposal posed photos.

Jonathan Heisler Photography is comprised of New York City photographers specializing in photographing private NYC proposals, as well as engagement sessions and weddings.

LEARN MORE ABOUT HIRING A PROPOSAL PHOTOGRAPHER IN NYC