Puerto Rico knows how to celebrate, but the engagement party of Thomas J. Henry, one of the most prominent personal injury attorneys from Texas, and Dr. Elena Álvarez-Westwood, one of Puerto Rico’s most respected doctors in women’s health, was something greater and magical.
The couple celebrated on Friday, December 5th, at the Fairmont El San Juan Hotel, where Elena’s Puerto Rican culture was present in all the best ways. The night was packed with friends and family, and full of the kind of warmth only the island can bring.
"We met in Puerto Rico, and this has been our special place. We have enjoyed so many times here and felt that it was most appropriate to share our engagement party with our family and friends."
From the moment guests entered the softly lit ballroom, adorned with tropical florals, modern design, and a rising sense of anticipation, it was clear this was not just another party, but an extraordinary event. It was a celebration where a story of love and Puerto Rican pride stood side by side, closing out 2025 with one of the year’s most unforgettable nights.
A Grand Party
The celebration at the historic oceanfront property began long before guests reached the ballroom. A 50-foot harp installation floated above the hotel lobby, where Earth Harp performed live as guests arrived and passed beneath the illuminated strings. It felt like something out of a movie.
Inside, palm-shaped ice sculptures framed a raw bar overflowing with oysters, shrimp, scallops, octopus ceviche, lobster tails, and more. A caviar station also featured Kalluga, Golden Osetra, and Paddlefish. Plus, another culinary highlight of the evening was lechón a la vara, a pillar of Puerto Rican festive culture.
Music filled the cocktail reception, led by Puerto Rican maestro Cucco Peña and 35 musicians from the Philharmonic Orchestra of Puerto Rico group performing contemporary selections by Carlos Vives, Andrea Bocelli, and others, a truly “unplugged” experience.
Fashion: Elena as the Night’s Shining Star
It was impossible to miss Dr. Elena Álvarez-Westwood. Her presence anchored the evening. A leader in early breast cancer detection and one of Puerto Rico’s most trusted figures in women’s health, Elena honored her beloved Puerto Rico with a series of wardrobe changes that became a highlight of the night.
She wore four gowns. One of the dresses was designed by Puerto Rican designer Gustavo Arango, a close friend who introduced the couple and still jokes that he deserves the credit for their love story. The other three were couture by Zuhair Murad, flown in from Paris for the occasion. Each gown brought out a different facet of Elena’s identity, from her Ponce upbringing to her unmistakable glamour.
Her hair and makeup completed her stunning look. Celebrity makeup artist Hung Vanngo, known for his work with Selena Gomez, created a luminous finish, while Eddy Scudo of The Wall Group styled her hair with soft, polished elegance.
Meanwhile, Thomas also looked elegant as he moved through the room in a polished look, a suede-style jacket with refined detailing, that struck the perfect balance of sophistication and ease, allowing Elena to stand out as the glowing goddess of the night.
A night of Iconic Latin Stars
Before the performances began, the ballroom went quiet as Elena and Tom made their entrance. They opened the dance floor with their first dance to “My Baby,” by Marc Anthony, a song they describe as the perfect reflection of their love story. Thomas then took the microphone to welcome guests and set the tone for the surprises ahead, before the night erupted into a stadium-level lineup.
Then, Marc Anthony opened the night and immediately ignited the room. His undeniable salsa energy filled the space as he performed his legendary hits, such as "Vivir mi vida" and "Ahora Quien". Guests danced and sang, while his rhythm reminded everyone why he remains one of the most powerful performers in Latin music.
Enrique Iglesias followed with a set that blended his charisma with an intimate connection to the crowd. From the first note, as he moved through hits like “Bailando,” “Duele el Corazon” and “Heartbeat,” drawing everyone in the audience, guests of all ages. Midway through the performance, the couple stepped onto the stage, joined by the dear friend who had first brought them together. Thomas spoke from the heart, saying that love at first sight still exists, even in your 60s, and reminding everyone that love is out there waiting, as long as you never lose hope.
Enrique embraced the couple before letting the music take over again. Between songs, with a playful smile, he asked them about their wedding date. They laughed and admitted that it had been intended to remain a secret at first, but they hinted that it might take place on April 4th, the day they first met. Because the engagement celebration took place on Dr. Alvarez-Westwood’s birthday, the night felt like a double celebration.
Ricky Martin closed the special performances, arriving with the kind of explosive energy that only he can deliver. Joined by a group of dancers, he launched into a high-powered set that instantly turned the ballroom into a dance floor. When he performed “María”, “She Bang”, and “Livin’ la Vida Loca”, making the evening feel larger than life.
Midway through Ricky’s set, another unforgettable moment unfolded. A towering red birthday cake was rolled out, and Ricky led the entire crowd in singing Happy Birthday to Elena. Each star added their unique layer to the celebration, turning the evening into something that will be talked about in San Juan for years.
"I have known Ricky for a very long time so having him sing happy birthday to me was very special. Being able to share this with Tom, our family and friends was a very warm experience I will never forget."
Puerto Rico Love and Pride
As the last notes of Ricky Martin faded, a traditional Puerto Rican folkloric band swept onto the dance floor, dressed in vibrant cultural attire. They led guests into a lively, parade-style celebration, a true paranda, complete with vejigantes and cabezudos, the island’s iconic masked characters and oversized papier-mâché figures that appear in the most joyous festivities, like their carnival. Guests followed the musicians as the celebration spilled into a spontaneous wave of island pride that carried everyone, locals and visitors alike, into the heart of Puerto Rican tradition.
As guests left the ballroom, men and women on tall stilts appeared at the doors, dressed in vivid local costumes. Once outside, beneath a sky scattered with stars, the band set up by the pool and continued with bomba and plena, the percussion-driven musical traditions of Puerto Rico. These music genres, often mentioned together yet distinct in rhythm, carry the island’s African heritage and inspire all who hear them to dance.
This living celebration became the backdrop for a breathtaking drone show that illuminated the night sky and narrated the couple’s love story. Light formations danced above the guests, shaping images of the couple dancing, playful messages like “She said yes,” and a cityscape symbolizing the connection between Texas and Puerto Rico. Palm trees, engagement motifs, and scenes from their journey together unfolded with luminous precision.
Every detail of the night was carefully curated to reflect not only Thomas and Elena’s love for each other, but also Elena’s deep affection for her hometown of Ponce, Puerto Rico. Guests also discovered little touches throughout the evening, such as a custom cocktail napkin printed in Elena’s favorite color, red, featuring a handwritten-style message from Tom that read: “Happy Birthday to the love of my life Elena, Love Tom.” A gesture served both as a tender declaration and a playful homage to Tom’s successful legal career, and to the old tradition of drafting agreements on bar napkins, a nod to a time when ink and instinct sealed the deal.
Beyond the glamour, the couple’s love story is also rooted in purpose. According to the press release, one of the most meaningful outcomes of their romance is their hope to continue expanding their philanthropic work across Puerto Rico, supporting post-earthquake recovery efforts in education services in Guayanilla, and serving as title sponsors of the American Cancer Society Puerto Rico Gala.
"Tom has been very helpful and helping me support causes that I know are important, not only for Puerto Rico but also nationally. I look forward to pursuing these philanthropic endeavors with Tom as we journey together in our new life."
Continuing this thoughtful storytelling, guests departed with gifts that truly showed Elena’s love for her culture: a bottle of Don Q rum from Ponce, honoring the city where she was born, and Montadero chocolate crafted from 100% Puerto Rican cacao. These details made the entire evening a love letter to both their story and the island that shaped it. As they look ahead to their wedding, the evening felt like the perfect beginning to their next chapter. It was the kind of night guests will remember for years to come.
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