Cailyn Henderson & Chandler Whitmer
Married
Jun 23, 2026
Brooksville ,
Florida
Photo Credit
Susan Elizabeth Photography
Style Guide
Color Palette
Style
Season
Summer
The Proposal
Chandler and Cailyn officially met in Indiana in December 2025, but their story began a few years earlier. Chandler had reached out to Cailyn on Instagram, and while she would respond occasionally, she never thought much of it at the time. Then, one day in December, Chandler appeared on her page again. Remembering that he lived in Indiana, Cailyn decided to message him. Eventually, she gave him her number, he planned their first date, and they never looked back.
Reflecting on that time, Cailyn believes God’s timing was behind it all. If they had met a few years earlier, they might not have been ready for one another. But when they finally came together, it was the right person at exactly the right time. By their second date, Cailyn knew Chandler was going to be her husband.
At the time, Chandler was the quarterbacks coach at Indiana University. Shortly after they met, he accepted a position as quarterbacks coach for the Tampa Bay Buccaneers. In April, Cailyn left her parents’ home in Indiana and moved to Tampa, trusting that God was leading them toward a life together.
While Chandler was helping Cailyn pack, she opened one final drawer and discovered a small, folded piece of paper. On it, she had written a prayer asking the Lord to show her who her husband was and to make it fully known and clear to her. When she unfolded the note, Chandler was sitting directly in front of her on her bed, helping her prepare for the move. She looked from the prayer to him and thought, “This is a God thing.”
When Cailyn and Chandler looked at engagement rings, she shared only a few preferences: an oval diamond, a delicate band, and some type of halo. Chandler suggested an under-halo and designed the ring himself. Amazingly, it looked almost identical to the only engagement ring Cailyn had ever saved—a photo she had kept for six years.
Cailyn suspected Chandler might propose over Memorial Day weekend, but Chandler surprised her the week before. They woke around 5:30 one morning for one of their usual sunrise walks along Bayshore Boulevard in Tampa. About 20 steps into the walk, Cailyn noticed a photographer near the water but assumed she was there to capture the sunrise. Moments later, Chandler turned toward Cailyn, and she immediately knew. He referenced one of their favorite sayings—“Forever ain’t long enough, so we might as well start now”—before getting down on one knee. Cailyn was so happy that she hugged Chandler before he could even place the ring on her finger. With the ring still in his hand and the water nearby, Chandler was silently thinking, “Please don’t drop the ring!” They were both shaking, and even Chandler, one of the calmest and most confident people Cailyn knows, had a tremble in his voice.
Cailyn and Chandler spent the next couple of hours drinking coffee on Davis Islands, FaceTiming their families, and soaking in the excitement. Then came the less-than-perfect part of their proposal day: Chandler had to drop Cailyn off at the airport for a work trip that would keep her away for several days. All they wanted was to stay together and celebrate, so saying goodbye was tough. At the same time, they could not help laughing at how terrible the timing was.
Their relationship may have moved quickly by the calendar, but it never felt rushed in their hearts. From the beginning, they felt God’s hand in their story.
In Preparation
Because of Chandler’s NFL schedule, they could marry before football season began or wait until the following year. They looked at each other and thought, “What are we waiting for?” They chose June 23—Cailyn’s birthday—and planned the wedding in one month.
Cailyn and Chandler initially considered Banff or California. Then, while playing golf at Cabot Citrus Farms, Chandler’s mother suggested that they marry there. They instantly knew it was perfect. Cabot had become their home course and a meaningful part of their relationship, not only because of its beauty but also because of the genuinely kind people they had met there. Although Cabot does not typically host weddings, the team graciously agreed to welcome their intimate celebration. Even more providentially, Dannah, a member of the Cabot team and a former wedding planner, offered to coordinate everything. With the help of Dannah, their mothers, and the entire Cabot team, it all came together beautifully.
Because they planned the wedding in only one month, Cailyn and Chandler decided to keep the celebration small and invite their immediate families. Family means everything to Chandler and Cailyn, and having such an intimate gathering allowed everyone there to spend meaningful time together.
Their rehearsal dinner took place outdoors beneath string lights and included archery, clay shooting, axe throwing, their favorite foods, and s’mores. It was fun because Chandler and Cailyn had never thrown a football together, so they finally got to do that!
With only a few weeks to shop, Cailyn needed to find a wedding gown off the rack. She chose a timeless strapless dress from David’s Bridal—completely different from the high-necked satin style she had always envisioned, yet somehow perfect. So many decisions were made at the last minute, but it felt as though God continued placing exactly what they needed in their path.
The Big Day
Cailyn and Chandler began their wedding day in the most fitting way possible: on the golf course. Cailyn played 18 holes on The Roost with her dad, while Chandler played Karoo with his dad and Cailyn’s brother. Spending that time with her dad on the morning of her wedding was something Cailyn will always treasure.
Although Chandler and Cailyn had planned not to see each other before the ceremony, it was also Cailyn’s birthday—the first one they had ever celebrated together—and they missed each other. They decided to spend a quiet 15 minutes together while Chandler gave Cailyn her birthday gift. It became one of the sweetest moments of the day.
Cailyn’s dad drove her to the ceremony in Cabot’s large black golf cart, which they affectionately called “the Batmobile.” Cailyn and Chandler were married beneath beautiful trees, in front of a wooden cross that Dannah’s dad had hand-built for them and inscribed with their favorite Bible verses. A violinist played some of their favorite Christian music, and they exchanged vows they had written themselves. Cailyn had never imagined writing her own vows, but their emotions felt too genuine not to express in their own words. Chandler is not typically an emotional person, so seeing tears in his eyes during the ceremony is a moment Cailyn will never forget.
Afterward, Chandler and Cailyn played a hole of golf in her wedding dress and his tuxedo and shared it as their first “newlyweds” golf video. They ended the day with an intimate candlelit dinner at one of Cabot’s cottages, surrounded by their immediate families.
Every part of the celebration reflected what mattered most to Cailyn and Chandler: their faith, their families, their love of golf, and the covenant they were making before God.
The Retreat
The following morning, Cailyn and Chandler left for Lake Tahoe. They wanted somewhere with the mountain beauty of Banff that they could plan quickly within the United States, and Tahoe was perfect. Cailyn and Chandler played golf, rode Jet Skis on the freezing lake, searched for new iced-coffee spots, and hiked Maggie’s Peak. Cailyn had no idea how high the hike would take them, but reaching the top together made it even more memorable.
Their honeymoon eventually became several weeks of travel. From Tahoe, they went to Denver for a GolfNow work trip where they did course reviews, then traveled to Georgia to celebrate the Fourth of July with Chandler’s family before visiting Cailyn’s in Indiana.
It felt like one long newlywed adventure filled with golf, iced coffee, and time with family. Most importantly, it allowed Cailyn and Chandler to enjoy their first weeks of marriage before Chandler’s football season began.
From an Instagram message that arrived before its time to the folded prayer Cailyn discovered while packing for Tampa, God’s hand was present throughout their story. Everything happened quickly, but it happened with certainty—and they would not change a thing.
Hallmark Wedding Vendors
Photography: Susan Elizabeth Photography
Contributing Vendors
Venue: Cabot Citrus Farms, cabot.com/citrusfarms
Coordinator: Dannah Bradel, @cabotcitrusfarms
Videography: Pine & Forge, @pineandforge.com
Hair: Amelia Walker, @hairbyameliarenee
Makeup: Stephanie Ruiz, @kissandmakeupbysteph
Florist: Bianca Regusa @bloomingstemsco
Dress: Oleg Cassini @olegcassini
Violinist: Ben Derrico, @thirdeyestrings
Officiant: Joran Price
