ISLAND WEDDING
Playful banter sparks lasting love for William and Lisa-Gaye
Published:Tuesday | March 10, 2026 | 12:06 AMRuth-Ann Briscoe/Gleaner Writer
For Lisa-Gaye Shakespeare and William ‘Billy’ Grant III, a playful rivalry between basketball fans unexpectedly turned into a love story that would cross both countries and cultures. They first met in May 2018 at a Miami sports bar during the NBA play-offs. She was proudly cheering for the Miami Heat, he was firmly rooting for the Boston Celtics, and as expected, their conversation started with some friendly ribbing. Lisa-Gaye recalls being immediately intrigued by William’s confidence.
“My first impression was, ‘Who is this man bold enough to walk up to me and start talking smack about my team?’” she recalled the moment to Island Wedding. “He wasn’t intimidating, he was playful, quick-witted, and completely comfortable in his own skin. I found that very attractive. Underneath the trash talk, I could tell he was smart, self-assured, and genuinely interested in the conversation.”
Their playful banter quickly gave way to an engaging conversation, igniting a spark as William found himself immediately drawn to Lisa-Gaye.
Intrigued by her beauty, William shared that, “There was an authenticity about her. The way she carried herself, the confidence in her voice, the way she owned her space, it was magnetic.”
He continued, “She lit up the room. I noticed how connected she was with her friends [and] how warm and present she was with the people around her.”
Only a week after their first encounter, William returned to Miami to take Lisa-Gaye on their first official date at La Mar by Gastón Acurio, a Peruvian restaurant in downtown Miami. After dinner, they spent the night bar hopping and dancing together.
“It felt effortless,” Lisa-Gaye shared. “No awkward pauses, no forced small talk.” William agreed, adding, “What stood out most was how natural everything felt.”
But it was their second date that confirmed the relationship was something truly special. The couple took a bold step early on, travelling together to Croatia for two weeks.
For Lisa-Gaye, the trip revealed a connection that felt rare and deep, “We explored new cities, tried new foods, danced, talked for hours and truly got to know each other.I remember thinking, ‘Okay… this is different.’”
William recalls that the trip marked a turning point for their relationship.“The way we laughed together, the way we naturally vibed, it just felt easy,” he said.
Over time, their connection became even more meaningful, and for Lisa-Gaye, one especially memorable moment came during a visit to William in Connecticut. He had planned a romantic weekend getaway at Winvian Farm in Litchfield.
“I remember thinking how rare it is to be with someone who doesn’t just show up, but creates moments,” she said.
William, however, felt that he realised his deep feelings even earlier, during their trip to Croatia. For him, everything had simply felt easy.
Like many relationships, theirs faced its own share of challenges. Long distance was especially difficult in the early stages, particularly when Lisa-Gaye returned to Jamaica and work commitments required frequent travel.
Long distance isn’t easy,” Lisa-Gaye admitted. “It forces you to communicate better, trust deeper and choose each other intentionally every single day.”
William agrees that communication was key throughout that time. “We didn’t ignore the hard conversations,” he said. “We had them.”
ROAD TO ‘I DO’
In February 2024, William planned a surprise proposal during Lisa-Gaye’s birthday trip to Jamaica. The couple were staying at Half Moon Resort in Montego Bay. Lisa-Gaye thought they were simply heading to dinner when William unexpectedly blindfolded her and guided her onto a golf cart. When the blindfold came off, she saw her mother, stepfather, and best friend waiting nearby. Moments later, William dropped to one knee.
“I was completely shocked in the best way,” Lisa-Gaye said, adding, “Without hesitation, I said, ‘Absolutely yes!’”
The couple exchanged vows on November 7 of last year at Elizabeth Park in West Hartford, Connecticut. Unlike the larger celebration they had originally planned, the ceremony was simple and heartfelt.
“There was no big production, no chaos,” Lisa-Gaye explained.
With only their photographer, Norman Oates, and officiant, Edward Sanady, present, the pair exchanged vows and rings, sharing their first kiss as husband and wife as the sun set around them.
Rather than a traditional reception, Lisa-Gaye and William chose to spend their special evening giving back. They participated in a television interview to raise funds and collect relief supplies to send to Jamaica, following Hurricane Melissa, which had affected their original wedding plans. Later, they shared a quiet celebration of their own with dinner and champagne, savouring the first moments of married life together.