Lifestyle August 18 2026

Island Wedding | Kasi Simon gets cuffed by Officer’s love

Updated 3 hours ago 4 min read

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  • Shawn Officer has Kasi Simon under arrest for love. The two joined hands in holy matrimony on June 13. Shawn Officer has Kasi Simon under arrest for love. The two joined hands in holy matrimony on June 13.
  • The Officers share a private moment before their wedding ceremony. The Officers share a private moment before their wedding ceremony.
  • The beautiful bride is escorted down the aisle by her son, Obryan Millwood. The beautiful bride is escorted down the aisle by her son, Obryan Millwood.
  • What started with a random phone call through a mutual friend blossomed into a romance. What started with a random phone call through a mutual friend blossomed into a romance.
  • In the presence of friends and loved ones, the newly-weds share a classic romantic dip kiss. In the presence of friends and loved ones, the newly-weds share a classic romantic dip kiss.
  • Mr and Mrs Officer look forward to spending the rest of their lives together. Mr and Mrs Officer look forward to spending the rest of their lives together.
  • Introducing the Officers’ wedding party. From left are groomsmen Dwayne Mendez, Davar Chambers, Ras Whitely, Linval Officer and Rushawn Johnson, followed by bridesmaids Natasha Brown, Brionnah Robinson, Sanique Percy, Nisha Nun and Marcie Lafrance. In th Introducing the Officers’ wedding party. From left are groomsmen Dwayne Mendez, Davar Chambers, Ras Whitely, Linval Officer and Rushawn Johnson, followed by bridesmaids Natasha Brown, Brionnah Robinson, Sanique Percy, Nisha Nun and Marcie Lafrance. In the front row are (from left) ring-bearer Rushawn Officer, the newly-weds and flower girl Ashawna Officer.

From the tender age of eight, Kasi Simon had already planned her dream wedding. She imagined her Prince Charming coming to save her, much like Rapunzel in her tower. Years later, her wish came true when her knight in shining armour, Shawn Officer, came into the picture. She had sworn off dating at the time, but was soon cuffed by this Officer’s love. Not long after, the couple joined hands in holy matrimony at Trident Castle in Portland.

As Kasi chatted with her compadre over the phone, Shawn stood in the background, curious about who was on the other end of the line. While Shawn was intrigued and further encouraged by the same friend who shared that he found him a wife, Kasi was busy renouncing any idea of romance.

“I was in the phase of my life where I had given up on love. I hadn’t dated in almost two years. When Shawn heard me and asked about me, I told our mutual friend that I wasn’t interested at all,” she explained to Island Wedding.

But her future beloved remained consistent in his pursuit. Over time, she agreed to give him her number. “Shawn didn’t hesitate to message me right away. Of course, I didn’t reply until a few weeks or messages later. Hey, you have to let these men chase you a little,” Kasi said with a laugh and a wink.

After getting to know each other better, the mutual friend was able to orchestrate a date and time for the pair to meet. “When I saw Kasi for the first time that September, I knew she would have been my wife. We went to a restaurant called Oceano with her and a friend. Not only was she the most wonderful person I have ever met, [but] she was also the most caring, optimistic, and sweetest person ever. I wanted to be in a relationship with her from that day forward,” Shawn said. But Kasi needed a little more time.

The pair became an official couple over a year later, in December of 2024.

Shawn appeared reserved and shy at first, but Kasi was drawn to his humility, kindness, protective nature and the active role he played as a provider.

“He is very intentional when it comes to his actions. I’ve learned to be more patient with others and not react to everything because of him. He nurtures our relationship by sending flowers to my office and planning dates. One of our most memorable ones to date was one he arranged by the beach. He did this without my knowledge and worked with an event planner to make sure the set-up was beautiful. It was one of the most thoughtful things anyone has done for me,” she highlighted.

As a couple, according to Kasi, they love watching movies for hours, travelling together, and trying new restaurants. “If I had to pick one of our favourite restaurants, I would pick Oceano because of her love for sushi, and that was where we first met and had our first date,” Shawn said, chiming in.

He knew Kasi was beautiful from the first time he saw her, but continues to be inspired by her kindness, thoughtfulness, caring nature and the way she supports her loved ones.

“She showed me how much she really cared by taking care of my daughter when she was sick and showing up for my sister’s graduation, despite it putting her out of her way,” he said, adding, “She loves to travel and try new things with those around her. This made me try new things like sushi or going on a ferry and visiting new countries like Antigua and the Bahamas.”

With her presence, he not only discovered a new meaning to life but also found someone he knew would always have his back. Her explanations gave him a better understanding of the world, completely changing his perspective. She also has a way of bridging the gap in their long-distance relationship through effective communication and frequent visits.

In May of the following year, Shawn took his soulmate to a restaurant in Mandeville where she received the surprise of a lifetime. “I told Kasi that I was going to the bathroom when I snuck off to give the waiter the ring and inform them that I would like to have a special moment to propose to her. The waitress wrote the message ‘Will you marry me?’ on the plate with the cake and the ring, along with sparklers. When she came out with the ring, she brought Kasi around the table, and that’s when my love realised that I was proposing.”

“The proposal was everything. My heart dropped when I looked over [and]there was a ring; I almost died,” Kasi confessed.

NUPTIAL MODE

She jumped right into nuptial mode, planning her own wedding. It was a stressful but rewarding experience. “I was determined to have the wedding of my dreams. I walked into Trident Hotel back in 2016, turned to the person I was with and said, ‘I am getting married here’. Mind you, I didn’t have the man yet or the proposal, but I knew immediately I wanted to get married in this castle one day,” she explained.

And the duo did just that on June 13, surrounded by specially invited guests, with the ceremony taking place on the front lawn overlooking the ocean, followed by a reception in the grand ballroom.

The dashing groom admitted that the wedding was the best moment of his life: “It was all that I had hoped for because I got to marry the love of my life around the people that matter the most. My favourite moment was when we both said our vows and I finally got to kiss my wife.”

For the gorgeous bride, the wedding was all that she prayed for: “All of our favourite people were in attendance. The best moment was dancing with my husband while the saxophonist played Save the Best for Last by Vanessa Williams. It was as if no one else was in the room with us. The inner child in me was proud.”

krysta.anderson@gleanerjm.com