Blueprint for Love

Emily Shaw and Brian McInnis

On her way to a 2014 Sarasota Architectural Foundation event, Emily Shaw, then 26, popped into Legends Sports Pub to meet some friends. That’s where she encountered building contractor Brian McInnis, then 27. Sparks flew.

“I shared my architectural knowledge on dates to Sarasota MOD Weekend 
while walking through home tours, and Brian shared his enthusiasm about the bones of a house,” says Shaw. McInnis proposed under the banyan trees at The Ringling and the couple got married at the Umbrella House, one of Shaw’s favorite Sarasota buildings. When they’re not sprucing up their well-preserved 1940s home, they and their 3-year-old son, Charlie, visit both the Ringling Museum and the site of their wedding to relive their happy memories.

High School Sweethearts

Francis Zamora and Nathan Rakay

Francis Zamora and Nathan Rakay met during their freshman year at Cardinal Mooney Catholic High School. They became close, and Rakay asked Zamora to be his girlfriend in front of the Unconditional Surrender statue on the Sarasota bayfront. “He blindfolded me, then gave me a dozen roses and jokingly yelled, ‘We’re getting married!’ to the crowd clapping around us,” says Zamora. Rakay attended college in Boston while Zamora studied in Gainesville. The pair split due to the distance but reconnected in 2019. Then, around the start of the Covid-19 pandemic, Zamora moved from New York City to Sarasota and they’ve been together ever since. Newly engaged, they enjoy outdoor adventures with their dogs and will get married this year.

Meet Cute

Brian and Matt Craft

In 2014, New York actor Brian Craft, then 24, came to Sarasota for a role in a short film. During the production, he met film extra Matt Yauslin, then 25. They had instant chemistry and went on their first date at Clásico in downtown Sarasota. They had been dating for two years when Matt asked Brian to meet him after rehearsal for some impromptu drinks—Brian was unaware that Matt planned to propose that night. “I was exhausted from rehearsals and didn’t pick up any hints, so I was authentically surprised,” says Brian.

The couple got married in 2018 at the Powel Crosley Estate. Whether they’re sipping espresso martinis at Cafe BarBosso or attending festivals together, the Crafts live out their love story against the romantic backdrop of Sarasota.

The Art of Love

Marco Bell and Monica Spain

Artists Marco Bell, then 43, and Monica Spain, then 41, met in 1998 while both were painting in the Edson Keith Mansion at Phillippi Estate Park. They bonded over their shared passion for art and began collaborating. Bell proposed a year later, and in 2000 the pair wed in the rose garden on the Ringling grounds, which they decorated with painters’ palettes. After a brief stint in New Orleans, they moved back to Sarasota and founded Bella Arte Studio in 2005.

“Our clients waited to see if we’d start arguing during a project,” say the couple, “but we’re each other’s good luck charms and love sharing ideas.” The pair, now 67 and 66, just completed a project at The Ritz-Carlton and continue to paint the town red together.

Creative Connection

Matteo Caloiaro and Brooke Olivares

Artists Matteo Caloiaro, then 23, and Brook Olivares, then 22, met in 2006 as students at Ringling College of Art and Design. After graduation, Olivares moved to San Diego while Caloiaro stayed in Sarasota, but they kept in touch online and struck up a friendship. When Olivares invited former classmates to participate in an art show at her church, Caloiaro was delighted to participate.

“Brooke freaked out, because I had already bought my tickets and then the show was rescheduled, but I kept my plans because I wanted to see her,” Caloiaro says. The two began a long-distance relationship before Caloiaro relocated to California, where the pair tied the knot in 2012. They returned to Florida to teach at Ringling and are now parents to children Sofia and Santino, with whom they share a colorful life in Sarasota.

Coming Home

Jewel and Kasey Truman

Kasey Truman, then 26, and Jewel Johnson, then 24, met through mutual friends at a 2014 LGBTQ+ festival in Orlando. They hit it off, but Jewel was about to embark on an exchange trip to Spain and hesitated to jump into a relationship. When Kasey asked her to be her girlfriend, Jewel turned her down. However, a stranger convinced Jewel to take the plunge. A year later, Kasey proposed in a magical recreation of their first date at a Christmas-themed bar.

Over the next three years, they deepened their relationship, moving to California, backpacking around Europe and returning to Bradenton, where they got married. “We met in Orlando, but our connections were from Bradenton and Sarasota,” say the couple, who now reside in Bradenton with their baby Apollo.