Molly and Michael: An Engagement in the Charm of Old San Juan

Romantic sunset silhouette of couple embracing on coastal cliff.

When Molly and Michael decided to take one of the most important steps in their lives, Puerto Rico became the perfect setting for their engagement. This story begins with an unexpected call from Michael, who reached out to me after receiving a recommendation from my dear friend and colleague Camille Fontánez. Filled with excitement, Michael shared all the details of his plan to surprise Molly during their trip from Dallas, Texas, to the island.

The Special Reason Behind the Chosen Location


Although they both live in Dallas, Michael holds a strong emotional connection to Puerto Rico, having grown up in the city of Ponce. This place meant so much to him, and he wanted the proposal to have a meaningful touch in a significant location. Old San Juan, with its historic charm and romantic atmosphere, became the ideal spot for this unforgettable moment.

Close-up black and white photo of a sparkling diamond engagement ring on a hand.
Romantic sunset proposal scene by the water with palm trees in the background.

The Beginning: Plaza Felisa Rincón de Gautier


Our meeting point was Plaza Felisa Rincón de Gautier, also known as the Plaza of the Cathedral. This spot is one of my favorites to start sessions in Old San Juan due to its versatility and the various photographic routes it offers. From this location, the historic and colorful ambiance of the old city unfolds before us. I was with my assistant, waiting for Molly and Michael to arrive in their Uber. While we waited, you could feel the excitement and anticipation in the air. Once we received Michael’s message confirming their arrival, everything was set in motion. With a discreet signal, I made sure to be ready to capture the big moment.

A couple shares a tender moment on a charming Old San Juan street with colorful buildings.
Couple sharing a romantic moment in front of an orange wall with ferns in foreground.
Romantic moment captured between couple with black car and orange wall backdrop.
Couple embracing in front of urban building with plants in foreground.
Joyful moment on terracotta stairs with white dress and blue blazer.
Black and white intimate portrait of romantic embrace.

The Proposal Moment


As soon as they arrived at the plaza, Michael guided Molly to the center, where, without much delay, he popped the big question. Molly, visibly moved, responded with a resounding “Yes!” Her surprised expression when she noticed us, ready to document the moment, was unforgettable. After warmly congratulating them, we began their engagement session.

Romantic couple posing on yellow-walled steps in tropical setting.
Intimate moment between couple on historic stone steps with peach colored walls.
Couple holding hands on stone steps with colorful colonial architecture background.
A romantic couple dancing on stone steps in a colorful alleyway with yellow walls and traditional architecture.
A black and white portrait of a couple embracing on historic stone steps.
A couple sharing an intimate dance moment on stone steps in a monochrome setting.
An intimate black and white close-up of a couple sharing a tender moment.

A Photographic Journey Through Old San Juan


Following the proposal, we embarked on a journey through some of Old San Juan’s most iconic spots. We started near Hotel El Convento, where the colonial facades and architectural details provided a perfect backdrop for their portraits. We continued to Plaza de la Rogativa, a place that always inspires with its views of the bay, and finished at Paseo de la Princesa, where the evening lights began to add a magical touch to the session.

A couple poses against a decorative black door with brass studs in an elegant setting.
A romantic moment captured against an ornate black door with gold accents.
A couple in formal attire embracing in front of a studded black door.
A couple sharing a tender moment against an ornate black door with brass details.
A black and white portrait of a couple posing against a decorative door with metal studs.
A couple in blue and white attire sharing a loving moment against a dark studded door.
A romantic couple shares a tender kiss against a dark door with gold studs at a beautiful location.
A couple embraces by a historic domed turret overlooking the ocean.
A romantic embrace by an ancient stone turret with ocean views.
A loving moment shared at a historic fort overlook with dome architecture.
A tender embrace against the backdrop of a stone watchtower and cloudy skies.
A couple shares an intimate moment at a historic stone fort overlooking the sea.
A playful moment exploring a historic stone watchtower with ocean views.
A curved stone pathway leads through a tropical garden with an ornate pillar and lush greenery.
A romantic couple embraces at sunset by the ocean with soft clouds in the background.

An Unforgettable Experience


I remember that while we were taking some shots at the Plazuela de la Rogativa, Michael noticed another couple getting engaged down at Paseo de la Princesa. Without hesitation, he shouted from above, "Congratulations!" It was a unique moment that added a special touch to our session. Time flew by as we captured every moment, and before we knew it, night had fallen. Connecting with Molly and Michael was so effortless that I lost track of time. To close the evening, Michael invited us to a nearby restaurant to unwind and share a relaxed moment after the session.

A couple embraces and kisses during an outdoor photoshoot in elegant formal attire.
A black and white romantic moment captured against a stone wall by the waterfront.
A romantic dip pose on a beautiful tree-lined pathway with vintage lampposts.
A couple walks hand in hand down a scenic stone pathway lined with trees and lampposts.
A couple strolls together on a picturesque pathway surrounded by lush greenery.
A sunset embrace on a charming brick pathway surrounded by trees and vintage lampposts.
A couple sits together on a waterfront wall during blue hour with a harbor view.
A romantic sunset moment by the ocean with a turquoise railing and pink sky.
A stunning sunset portrait by the ocean with dramatic pink and purple sky.
A couple embraces on a waterfront terrace at sunset with pink and purple skies over the ocean.
A couple dancing under string lights at night in formal attire.
A romantic moment under twinkling lights with a couple in evening wear.

What’s Next


This engagement session in Old San Juan was just the beginning of a unique experience with Molly and Michael. Join me in the next chapter of this story, where I’ll cover every detail of their big day and the Brunch Day that wrapped up their celebration in Puerto Rico. Don’t miss it!