A Surprise Proposal During a Luxury Maternity Session at Hyatt Regency Grand Reserve, Puerto Rico

Luxury beach maternity photography session in Puerto Rico at sunset.

Every so often, a photography session evolves into something far deeper than portraits alone. It becomes layered with anticipation, emotion, and moments that quietly change the trajectory of people’s lives. That was precisely the case when Brendon, a bodybuilding athlete visiting from New Jersey, reached out after discovering my work. The initial plan was straightforward: a maternity session in Puerto Rico while vacationing with his girlfriend Sara. What he revealed shortly after, however, added an entirely new dimension. He intended to propose at the end of the shoot.

Blending maternity portraiture with a surprise engagement proposal is not something I encounter often, yet it immediately felt compelling. It offered the opportunity to document two profound milestones simultaneously, all within the stunning setting of the Hyatt Regency Grand Reserve Puerto Rico, one of the island’s most elegant resorts and a venue I’ve grown especially fond of for weddings, elopements, and destination portrait sessions.

Discreet Planning Behind the Scenes

Romantic destination couple portrait with soft natural Caribbean light.

Executing a surprise proposal within an already emotional maternity session requires careful orchestration without ever disrupting the natural experience for the couple. Brendon collaborated with my good friends at I Do Proposal, who designed a minimalist, romantic beachfront setup that complemented the surroundings without feeling staged or excessive. The goal was intimacy, not spectacle.

Maintaining the element of surprise meant solving small logistical challenges quietly. My trusted contact at the resort, Pamela, graciously stepped in to retrieve the engagement ring beforehand under the guise of routine hospitality. That small act ensured Sara would remain blissfully unaware until the perfect moment arrived. Details like these often go unnoticed, yet they are essential in allowing authentic emotion to unfold uninterrupted.

Beginning the Maternity Portrait Session

Editorial maternity photography highlighting elegance and intimacy.

I arrived early to scout light and confirm the exact proposal location. The decorators had chosen a beautiful spot near the water, subtly different from our original plan yet visually stronger, offering both privacy and a breathtaking coastal backdrop. When I finally met Brendon and Sara outside their suite gazebo, their connection was immediately evident. Some couples naturally carry a quiet chemistry that translates effortlessly on camera, and they were certainly among them.

Sara’s maternity dress elegantly highlighted her early baby bump in a way that felt refined rather than overt. We began the session near a grassy knoll and reflective pond, creating intimate portraits that emphasized tenderness over posing. I leaned into short lighting techniques to sculpt dimension and mood while allowing the lush Caribbean landscape to frame them softly. Those early moments set a relaxed tone that carried beautifully throughout the session.

Moving Toward the Beach With Editorial Intent

Surprise proposal captured during a destination portrait session.

As we gradually made our way toward the shoreline, I allowed the environment to guide the session organically. Small pauses along the path became opportunities for portraits that felt spontaneous rather than directed. One particularly striking image emerged through a natural gap in a tree where Brendon gently held Sara’s belly while leaning close. It was understated, emotional, and effortlessly elegant.

Upon reaching the beach, a massive Puerto Rican flag waving near a palm tree stump immediately caught my attention. Incorporating it into wide compositions added both scale and narrative context, transforming simple maternity portraits into something that felt cinematic and editorial. The movement of the flag, the ocean breeze, and the warm light created a sense of place that elevated the imagery far beyond standard destination portraits.

Preparing for the Proposal Moment

Timeless maternity portrait emphasizing natural beauty and movement.

Timing a proposal within a portrait session is always delicate. There is a balance between allowing anticipation to build naturally while avoiding any sense of awkward delay. At one point, I asked Sara to turn back briefly for solo maternity portraits, which provided the perfect opportunity to discreetly pass the engagement ring back to Brendon. The added benefit was that these portraits turned out to be among the strongest of the session, thanks in part to Sara’s modeling background and her comfort in front of the camera.

As we slowly approached the decorated beachfront area, I kept conversation flowing in a relaxed way so the setup wouldn’t immediately draw attention. Eventually, intuition took over. Sara began sensing that something meaningful was about to happen. That shift in awareness often produces some of the most genuine expressions I capture.

An Emotional Beachfront Proposal

Destination photography session blending romance and storytelling.

When the couple stepped into the semicircle of flowers overlooking the water, I instinctively gave them space while remaining ready to document every second. Brendon spoke from the heart before getting down on one knee, and Sara’s reaction unfolded with beautiful authenticity. Tears, laughter, surprise, and joy blended together in a way no amount of posing could ever replicate.

Moments like these remind me why documentary-style photography resonates so deeply. Perfection isn’t the goal; truth is. Those fleeting emotional transitions are what couples revisit years later when they look back at their photographs.

After the initial excitement settled, I allowed Sara a few minutes to compose herself before transitioning into engagement portraits. The newly presented ring, elegant and timeless, naturally became part of the storytelling as they celebrated this new chapter alongside the anticipation of parenthood.

Ending With Editorial Portraits in Changing Light

Elegant couple portrait showcasing authentic emotional connection.

Just as we were wrapping up, a light Caribbean drizzle began drifting in. Rather than retreat, I leaned into the atmosphere by introducing off-camera flash to create dramatic editorial portraits against the fading sunset. The combination of soft rain, warm ambient light, and controlled highlights produced images that felt almost cinematic.

Unexpected weather often introduces character into photographs, and in this case it provided a striking, magazine-worthy conclusion to an already unforgettable session.

A Session That Celebrated Two Life Milestones

Sunset beach engagement photography with luxury destination vibes.

What began as a destination maternity session ultimately became a layered story about transition, commitment, and new beginnings. Documenting both pregnancy and a surprise engagement within a single evening presented creative and logistical challenges, yet it also reinforced why I’m drawn to this work in the first place. Photography has the unique ability to preserve not just events, but emotional thresholds.

Parenthood was on the horizon for Brendon and Sara, and their engagement marked another meaningful step forward. Capturing both milestones together created a narrative richer than either moment alone could provide. Experiences like this continue to affirm that the most powerful images rarely come from perfect conditions, but from genuine connection, thoughtful planning, and allowing life to unfold naturally in front of the lens.

And honestly, sessions like this are the kind of challenge I’ll gladly accept every single time.

A Sunlit Marriage Proposal at the Hyatt Regency Grand Reserve, Puerto Rico

The white heart-shaped arch adorned with sunflowers and yellow petals, ready for a magical proposal moment.

     When Myron first reached out to me about a month ago, he had a clear vision in mind: to propose to his girlfriend, Devon, in a way that was deeply personal and visually unforgettable. Just a month earlier, the two had welcomed a baby boy into their lives, so this proposal was about more than just romance—it symbolized the start of a new chapter as a family. He wanted to make the moment count, and he chose one of the most breathtaking venues for it: the Hyatt Regency Grand Reserve in Río Grande, Puerto Rico.

Why the Hyatt Regency Grand Reserve Was the Perfect Choice

Hidden behind the greenery, I waited for the perfect moment to capture Devon’s surprise.

     The Hyatt Regency Grand Reserve is not just another resort—it’s a destination known for its elegance, tropical scenery, and unparalleled service. Located along the northeastern coast of Puerto Rico, this luxury venue is surrounded by lush greenery, palm trees, and panoramic ocean views that make it ideal for engagements, elopements, and destination weddings. Its sprawling grounds, beachside gazebos, and refined architecture make it a dream setting for any proposal photographer in Puerto Rico. It’s no wonder couples from all over the world fly in to make their moments here truly unforgettable.

     For Myron and Devon, the choice made perfect sense. It offered the privacy and beauty of a secluded destination while showcasing everything Puerto Rico is known for—warm weather, breathtaking sunsets, and a romantic energy that never fades.

The Virtual Meeting and the Perfect Alibi

It’s the little things…

     Before the big day, Myron and I broke the ice during a virtual meeting. Devon happened to be shopping at a mall at the time, which gave Myron the perfect excuse to say he had a “client meeting.” In truth, I was that client. During our conversation, I got to learn more about their story—they’re from Cleveland, Ohio, and wanted to escape the freezing temperatures for something warmer and brighter. Puerto Rico, with its endless summer and natural beauty, was exactly what they needed.

The Planning and Design

Champagne in midair, laughter all around—a symbol of celebration and pure joy

     As the proposal date approached, Myron decided to elevate the experience by adding a decorative element to the setup. I recommended a few local planners and decorators I often collaborate with, and he chose to work with Katherinne Moreira, founder of I Do Proposals, an emerging proposal planning company in Puerto Rico. Katherinne’s design vision for the moment was stunning: a white arch in the shape of a heart, soft yellow petals scattered on the ground, and bright sunflowers interwoven throughout the structure. The result was a scene that felt intimate, elegant, and full of joy—just like Myron and Devon’s story.

Arriving Early and Setting the Scene

Their baby’s stroller in the background, a subtle reminder of the love that started it all.

     On the day of the proposal, I arrived early to capture photographs of the decoration and to finalize positioning. I sent Myron an edited image of the setup with two guiding lines: blue for him and pink for Devon. This small but crucial step helps me ensure everything aligns perfectly when the moment happens, taking into account wind direction, sunlight, and reflections—details that can make or break a proposal photo.

     The chosen spot was one I had discovered weeks earlier during a previous engagement shoot. Hidden, romantic, and perfectly lit, it was ideal for a surprise. As I waited behind a large bush, camera ready, I saw the couple approach—Myron pushing a baby stroller, Devon blissfully unaware of what was about to happen. Including the stroller in some of the photos felt important to me; it symbolized the family they had already begun building together.

The Champagne Moment and the Yes

A close-up of their hands and rings—two hearts joined forever

     When Myron finally reached the designated spot, he took a moment to gather himself before kneeling down. The proposal unfolded beautifully—pure emotion, no need for direction. There was a small hiccup when it came time to pop the champagne bottle, but with a quick tutorial on how to shake it just right, we got the cork to fly, filling the air with bubbles and laughter. Those shots—champagne midair, sparkling sunlight glinting off each drop—are among my favorites.

Chasing the Sunset

The Hyatt Regency Grand Reserve bathed in golden light as the couple embraces

     As the sun began to dip below the horizon, I checked my watch: 6:00 p.m.—right on schedule. I had already arranged for a golf cart to pick us up and take us to another part of the Hyatt for golden hour portraits. The sunset, however, seemed to move faster than usual that evening, so we decided to linger a bit longer around the lobby area to take advantage of the last remaining light.

The Final Location and Creative Lighting

Dangling lights overhead created natural leading lines that drew the eye to the couple’s connection.

     We stumbled upon an outdoor patio adorned with dangling lights that created beautiful leading lines overhead—a photographer’s dream. Behind it stood a majestic three-story fountain, cascading water illuminated by the soft ambient glow of the lights. To balance the lighting, I placed a flash behind the fountain and used a CTO gel to match the warm tones of the environment. The result was cinematic and magical—a perfect blend of technical precision and heartfelt storytelling.

Reflections on a Perfect Day

     The weather held up beautifully, the clients were an absolute delight, and the entire session unfolded effortlessly. What made this proposal truly special wasn’t just the setting or the decor—it was the authenticity of the moment. Myron and Devon’s connection was raw and real, their baby boy added an emotional layer of meaning, and the Hyatt Regency Grand Reserve provided a setting that elevated it all.

     Every engagement I photograph in Puerto Rico reinforces my love for storytelling through images. It’s not just about taking pictures—it’s about preserving fleeting emotions, crafting timeless visuals, and honoring the unique journey of every couple who trusts me to capture one of the most important moments of their lives.

     To Myron and Devon—thank you for allowing me to document your story. May your journey together, with your beautiful little boy, be filled with laughter, light, and everlasting love.

A Surprise Marriage Proposal at the Hyatt Regency Grand Reserve in Puerto Rico

The perfect setting: Josiah chose the Hyatt Regency Grand Reserve in Puerto Rico, one of the island’s most beautiful venues, for his surprise proposal to Rosie.

     Every proposal has a story worth telling, and Josiah and Rosie’s is one for the books. When Josiah reached out to me via my website about a month before his big day, I knew immediately that his vision was heartfelt. After selecting a virtual meeting through my contact form—a service I offer to make planning stress-free—we broke the ice online.

     During our chat, Josiah shared that he met Rosie not on Tinder, as I mistakenly thought at first, but on Twitter. Their connection grew steadily, especially during the pandemic, when they leaned on each other through the uncertainties of Covid and quarantine. After five years together, Josiah was ready to take the next step: a destination proposal in Puerto Rico.

Choosing the Hyatt Regency Grand Reserve in Río Grande

A love five years in the making: Josiah and Rosie met on Twitter and grew stronger together during the pandemic before saying “yes” in Puerto Rico.

     Josiah selected the Hyatt Regency Grand Reserve in Río Grande as the venue for the big moment. While the resort is also one of Puerto Rico’s most sought-after wedding venues, I’ve had the honor of capturing numerous proposals there. The tropical setting, lush greenery, and beachside sunset views make it an unforgettable backdrop for engagements.

Preparing for the Big Moment

She said yes: Rosie’s emotional reaction captured the surprise, joy, and love of the moment.

     I never approach a proposal without preparation. For Josiah, we did a quick phone rundown where I emphasized two important things: staying calm and not rushing the moment. Too many times, clients have knelt down almost instantly after walking onto the scene, leaving little room to capture the buildup. I reminded Josiah that soaking in the moment—the handholding, the teary eyes, the anticipation—would make the proposal itself even more powerful.

     Josiah was all in. Confident, steady, and sure about his decision. Since he also wanted video coverage, I arrived early on proposal day to scout locations. With input from my associate Carola and Hyatt’s on-site guide, Jacob, I discovered the perfect grassy area near Building 9. Framed by two large boulders, it felt private and symbolic—ideal for capturing a once-in-a-lifetime memory.

Behind the Lens: Planning the Shot

The moment is too good to not soak it in at the Hyatt Regency Grand Reserve

     I met Josiah briefly to rig him with a microphone, though his choice of a white linen shirt posed a challenge. Pro tip: a tank top under light fabrics makes it easier to conceal audio gear. Once he was ready, I set up my Canon RF 100mm f/2.8 for video and my go-to Canon RF 70-200mm f/2.8 for photography, ensuring I could capture intimate moments without intruding.

     As Josiah and Rosie strolled the sandy beach, I crouched behind a bush (a detail we laughed about later) and documented the buildup. Josiah spent nearly ten minutes speaking from the heart before finally pulling out the ring and dropping to one knee. Rosie’s reaction was pure joy—tears, hugs, and the sweetest yes.

Golden Hour Portraits

Golden Hour portraits: We headed to the west-facing beach to capture the newly engaged couple against Puerto Rico’s breathtaking sunset.

     After the excitement settled, I shifted into portrait mode. The newly engaged couple was still glowing from the proposal, which always makes for authentic, emotional images. Because daylight was fading, we arranged for a trolley to take us to a west-facing beach spot for golden hour portraits.

     The logistics weren’t seamless—the trolley was late, and I accidentally loaded into the wrong cart—but we eventually made it to the right place. There, I positioned Josiah and Rosie strategically to block background distractions, ensuring clean, distraction-free photos.

     With my Godox AD200 Pro II flash, I balanced the colors of the sky against the couple’s embrace, using both wide and tight shots with my Canon RF 15-35mm f/2.8. The tropical sunset did not disappoint.

Finishing at the Iconic Dome

An iconic finish: The proposal session ended at the Hyatt’s signature dome, with dramatic lighting that sealed the night with unforgettable images.

     No proposal session at the Hyatt Regency Grand Reserve is complete without a visit to the dome, a signature photo spot for photographers. While the structure’s many pillars can be tricky for lighting, I came prepared with a second flash—my Godox AD100 Pro paired with a CTO gel. This created warm, cinematic tones against the deep blue evening sky, wrapping up the session with a dramatic flourish.

A Quick Turnaround and Lasting Memories

     Within 24 hours, I delivered the full proposal gallery and video to Josiah and Rosie. Their story, from a chance meeting on Twitter to a destination proposal in Puerto Rico, reminded me why I love capturing these milestones. Every proposal is unique, but the joy, the anticipation, and the love are universal.

     If you’re planning to propose in Puerto Rico, whether at the Hyatt Regency Grand Reserve or another stunning location, I’d love to help you capture it. From planning guidance to professional photography and videography, I ensure every detail is documented beautifully.