Island Wedding | A decade-long journey to the Crossfields

The heart wants what it wants, and for Aleesha Brown and Shamar Crossfield, that led them to each other. Ten years after their paths first crossed in high school, the registered nurse and law graduand joined hands and hearts in matrimony on Saturday, May 23, at Hotel Four Seasons in St Andrew.
It was September 2016, and Aleesha and Shamar were starting third form at Ardenne High, where they shared the same form room. Their interactions were cordial, mostly limited to exchanging greetings, but by the end of the school year, those brief encounters had blossomed into longer conversations. They soon realised they would be sharing most of their Caribbean Secondary Education Certificate (CSEC) classes, and Aleesha was excited to be in the same class as someone she already knew.
“Shamar was someone I noticed since he would come early in the morning and arrange the desk and chairs in class, which said so much about his character, doing the things that no one sees. He seemed like a very genuine person but a bit reserved,” Aleesha told Island Wedding. 
For Shamar, Aleesha’s outgoing personality was what first caught his attention. “She was very involved, kind to everyone, and always positive,” he added.
By 2018, they were close friends who could talk about almost anything and had developed a deep understanding of one another. It was during this time that Shamar’s actions began to reflect how he truly felt about Aleesha.
“Shamar really demonstrates ‘actions speak louder than words’, He was consistently showing me how he felt by the things he did and how he treated me,” she explained. “He wrote me an extended love note because putting his feelings into words was a bit hard at first, and I could tell it was from his heart. I knew then at 17 [years old] that I was in love.”
Their relationship took a quiet turn on February 25, 2019. Amid the CSEC mock examination period, Aleesha decided to confess her feelings to Shamar: “The next day at school right after [our] exam, Shamar revealed he felt the same way and asked [me] to be his girlfriend.”
The couple had their first date at Palace Cineplex, where they watched the 2019 Marvel film Captain Marvel and shared their first kiss. Falling in love at such a young age, they experienced many of life’s changes while supporting each other every step of the way. For Shamar, falling in love with Aleesha came naturally because they had already spent so much time as close friends and knew each other so well.
Sharing what he loves the most about his favourite person, Shamar told Island Wedding, “I admire how caring and kind Aleesha is to everyone. She is a beacon of joy, radiating positivity to everyone she interacts with. I admire her ambition and how she gives her all to anything she’s involved in.”
Equally in awe of her partner, Aleesha describes Shamar as thoughtful, humble and hard-working: “He is reliable and shows up to help those around him. I love how creative he is and how hard he works on his craft – whether videography, YouTube, [or] editing, he really pours love into everything he does.”
It was one summer while Shamar was overseas and Aleesha remained in Jamaica that he knew he wanted to make her his wife.
“I was working overseas and was away from Aleesha. I missed her dearly. I truly wanted to ensure that she would forever be by my side,” he shared.  From that moment, he began planning the next chapter of their lives together.
SUMMER PROPOSAL
After months of planning the proposal on his own, Shamar sought the blessing of both their parents in July last year. With Aleesha’s mother secretly helping him get her ring size, he bought the exact ring his future bride wanted.
During the couple’s summer vacation, Shamar asked the love of his life to marry him on September 5, 2025, at the Grand Decameron in Montego Bay.
“I was nervous leading up to it, not because I thought she would say no, but because I did not want her finding out or getting suspicious about it before it happened. And, in the moment that I was about to get on one knee, my heartbeat sped way up,” Shamar recounted. 
Aleesha had just finished nursing school and had no idea it was coming. 
Shocked when it did, she shared that, “When he came back [from abroad], I did not expect there to be a proposal; I thought he was waiting ‘til he finished law school.” Aleesha continued, “I felt elated and simply overcome with joy. The moment felt right, and I trusted God with everything.”
In May this year, Aleesha and Shamar became Mr and Mrs Crossfield in an intimate ceremony at the Hotel Four Seasons, officiated by Bishop Dr Junior R. Headlam.
Waiting in her father’s car before the procession, Aleesha found a quiet moment for gratitude. “I was just thanking God for bringing Shamar into my life and that this ceremony was happening,” she added.
The wedding party walked down the aisle to American singer Haley Reinhart’s cover of Elvis Presley’s Can’t Help Falling in Love. Aleesha followed to an instrumental version of Turning Page by Sleeping at Last. Seeing his bride for the first time, Shamar was overcome with emotion.
“All I was thinking about was how much Aleesha and I have been through over the years — all the experiences we’ve had, all the different parts of each other that we’ve seen, all the family we’ve met. It all led up to this moment. And that was just the wedding party’s procession. But once I saw Aleesha come around the corner, it was wraps. I was a crying mess. She looked so beautiful,” he explained.
“Seeing him cry was quite shocking, but when I got there, I held him and told him ‘it’s okay’,” Aleesha said, chiming in.
The reception, held on the hotel grounds, was catered by the staff. To keep guests entertained, the couple organised a Kahoot! quiz at each table to see who knew them best.
Feeling the genuine support of her loved ones and friends, Aleesha admitted to getting emotional: “Seeing our family and friends and hearing speeches at the reception really got me teary-[eyed]. The support from our community has been a blessing.”
The couple’s first dance was to Shania Twain’s 1997 single You’re Still the One. They later celebrated their honeymoon at RIU Negril.
ruth-ann.briscoe@gleanerjm.com