A Sunset Rooftop Proposal on the Upper East Side: Dan & Chloe’s Love Story
There’s something undeniably magical about a rooftop proposal in New York City, especially when it’s timed perfectly with the golden glow of sunset. Dan and Chloe’s Upper East Side rooftop engagement was a perfect example of how simplicity, intention, and timing can create an unforgettable moment. As a NYC proposal photographer, I’ve seen all kinds of setups, but this one hit that sweet spot between relaxed and romantic. Here’s a behind-the-scenes look at how it all came together and some tips for planning your own rooftop proposal in New York.
The Backstory: Three and a Half Years of Love
Dan and Chloe had been together for three and a half years when he called me with a plan. He wanted to propose on the rooftop of their Upper East Side apartment building, where they’d spent countless evenings together. The idea was simple: no over-the-top props, no crowds, just a quiet, personal moment at sunset in a space that already held meaning for them.
From the very first call, Dan’s excitement was contagious. He knew what he wanted: a beautiful setting, a little champagne, and the ability to truly enjoy the moment with Chloe. And that’s exactly what we made happen.
Choosing the Right Location: Why Rooftops Are a Hidden Gem
New York is full of proposal spots, Central Park, the Brooklyn Bridge, the Top of the Rock. But rooftops offer something uniquely special: privacy, views, and a feeling of being above the noise of the city.
Dan and Chloe’s rooftop had it all, skyline views, a cozy layout, and that golden-hour light that photographers dream of. Best of all, it was their space. There’s something incredibly intimate about proposing in a spot that’s already part of your story.
If you’re considering a rooftop proposal, you don’t need to book a fancy rooftop bar or rent out an entire venue. Sometimes the best views come from your own building. Just be sure to check with your building’s management or landlord beforehand, and plan for potential weather backups if needed.
The Importance of Timing: Sunset is Everything
Timing a proposal around sunset is one of the easiest ways to elevate the look and feel of the moment. For Dan, that meant a bit of planning, sunset on the day of the proposal was around 8:00 PM, so we aimed to have Chloe up on the roof by 7:20PM.
We coordinated everything down to the minute. Dan told Chloe they were heading up to the roof for a casual evening drink, nothing out of the ordinary. I arrived a little earlier to set up and blend into the background, making sure I was in place when they walked out.
The light was soft and warm, casting a golden hue over the buildings and their faces. When Dan got down on one knee, it felt like the entire city paused just for them.
Keeping It Simple
If you’re wondering how to plan a rooftop proposal in NYC without it feeling like a huge production, here’s the good news: it doesn’t have to be complicated to be special.
Dan kept it simple:
A clean rooftop setup, no elaborate decor, just the natural beauty of the skyline.
A chilled bottle of champagne to celebrate the moment.
A few family members waiting downstairs to join in after the proposal.
That’s it. And it was perfect.
The focus stayed where it should be, on the connection between two people and the joy of taking the next step together. Sometimes less really is more.
Capturing the Moment: Documentary-Style Photography
One of the best things about Dan and Chloe’s proposal was how present they were. From the moment Dan dropped to one knee, to the champagne pop, to the shared laughter afterward, they were fully in it.
As a documentary-style photographer, that’s my favorite kind of moment to capture, genuine emotion, real expressions, and organic interaction. There’s nothing forced or overly posed, just the raw beauty of a life-changing question and an unforgettable "yes."
I moved around quietly, using the soft natural light to document every angle of their story without interrupting it. The result? A gallery full of timeless images that reflect exactly how it felt in the moment.
A Sweet Surprise: Family Joins the Fun
After the initial celebration, Dan had one more surprise up his sleeve—he’d invited both of their families to join them on the rooftop. Just a few minutes after the proposal, the door opened, and in came their loved ones, smiling, cheering, and ready to celebrate.
It was the perfect way to transition from private to shared joy. We spent some time taking group photos, capturing hugs, happy tears, and a few more glasses of champagne. Having family there added a layer of warmth and meaning that made the evening even more special.
Tips for Planning a Rooftop Proposal in NYC
Thinking about proposing on a rooftop? Here are a few quick tips to help you make it memorable (without the stress):
1. Scout the Rooftop in Advance
Make sure you know the layout, lighting, and access rules. If it’s your building, get permission if needed and clean up the space a bit beforehand.
2. Know the Sunset Time
Golden hour varies by season, so check the sunset time for your proposal date and plan accordingly. Arrive early so you're not rushed.
3. Keep the Setup Personal
You don’t need a flower wall or 100 candles. A blanket, a bottle of champagne, or even just a meaningful playlist can go a long way.
4. Have a Photographer in Place
Hiring a photographer (hi!) ensures the moment is captured without you having to worry about a tripod or selfie angle. I’ll be there early, hidden out of sight, and ready to document everything.
5. Consider a Follow-Up Plan
Whether it’s inviting family, heading to a dinner reservation, or simply enjoying a quiet moment together, think about how you want to celebrate after the “yes.”
Why I Love Rooftop Proposals
As a NYC proposal photographer, I’ve photographed couples all over the city, but there’s something special about rooftops. They feel private, elevated (literally and figuratively), and deeply personal. You’re above the noise, the pace, the chaos and left with nothing but the view, the moment, and each other.
Dan and Chloe’s proposal is one I’ll remember for a long time, not because of flashy decor or elaborate planning, but because of how authentic it felt. It was a reminder that the best proposals don’t need to be complicated, they just need to be real.
Looking to Plan Your Own NYC Proposal?
If you’re planning to pop the question and want someone to capture the moment discreetly and beautifully, I’d love to help. Whether it’s on your building’s rooftop, in Central Park, or somewhere totally unique to you, I’ll work with you to plan the timing, the lighting, and the logistics so you can focus on what matters, asking the biggest question of your life.
Reach out to book your NYC proposal photography today
