Our Story
Josylin and Jack met in 2020 during one of the most chaotic seasons of high school life, lockdowns, online classes, and endless uncertainty. Both had founded Turning Point USA (TPUSA) chapters at their Colorado high schools, something that wasn’t always easy or popular. When in-person meetings were shut down, Josylin, who was serving as president, organized a Zoom call with chapter leaders across the state to discuss how to handle backlash, stay active, and support one another.
The meeting began with someone hijacking the screen and blasting disruptive noises. Once that was handled, the introductions resumed, until Josylin noticed one attendee listed under the name “Wolfgang.” Assuming it might be another prank, she challenged him publicly, questioning whether it was even his real name.
It was.
Embarrassed, she reached out afterward to apologize. That apology turned into a Snapchat group chat for the TPUSA leaders, and then private conversations between the two of them.
At the time, Jack had recently moved back to Florida and was in a relationship. Their conversations were respectful and mostly centered around politics, school, and life. But even in those early exchanges, there was a natural ease between them. When Jack eventually returned to Colorado after restrictions eased and ended his relationship, knowing long distance wasn’t for him, Josylin was one of the first people outside his inner circle to know.
What began as occasional check-ins quickly turned into something more consistent. They started calling. Then they started calling every day. For nearly four months, they spoke constantly, about family, future plans, fears, faith, ambitions, and everything in between. There was no pressure to impress, no pretending, just comfort.
Neither had set out to fall for someone they had never met in person. But the connection was undeniable. Eventually, Josylin admitted she had feelings, knowing she might risk the friendship. Jack felt the same way.
They made one promise: they wouldn’t officially start dating until they met face-to-face.
That opportunity came when Jack and his dad had business in Denver. After accidentally boarding the wrong rental shuttle at the airport and walking nearly a mile with luggage to the correct one, they arrived 30–45 minutes late for the date.
When Josylin stepped out of the car and hugged him for the first time, it didn’t feel like meeting a stranger. It felt like coming home. There was no awkwardness, just peace. Even with both of their parents present that day, everything felt natural.
By the end of the date, they both quietly knew.
That night, neither of them slept much. At 3 a.m., Jack texted Josylin saying how good of a time he had. She responded instantly, she hadn’t been sleeping either.
The next morning, while his dad attended a meeting, Jack asked Josylin to be his girlfriend.
They officially began dating on February 1, 2021, knowing long distance would be part of their story for the next two years. This time, though, it didn’t feel uncertain. It felt worth it.
From weekend trips to Aspen, long bus rides across Colorado, stock shows, stable days, and countless visits back and forth, they built their relationship on intention, loyalty, and unwavering support.
From the very beginning, they were each other’s biggest cheerleaders, first chasing individual dreams, and now building shared ones.
2021
we were still in high school, figuring things out together and making the most of every chance we had to see each other. Between long-distance weekends—whether it was a three-hour Bustang ride or meeting up for trips—we learned how to make time count. It was also a meaningful year, as Jack was baptized, marking an important step in his faith. Like everyone else, we dealt with the ups and downs of COVID restrictions, but it never stopped us from finding ways to be together.
2022
we celebrated one year together in Aspen, worked the Stock Show, went to prom side by side, and both graduated high school. We attended a TPUSA event and spent long days working at the stables, building memories we’ll never forget.
In June, Jack moved to Florida for a summer program at USF, and by the end of August, Josylin followed, moving into his college dorm and starting a brand new chapter. Between Airbnbs and even nights in Jack’s truck, we figured it out together.
That same season, Josylin landed her first official job in Florida, and we began building our life from the ground up.
2023
Josylin got her first apartment, and we celebrated two years together. Jack spent the year building at the marina with Blake. When the six-month lease ended in June, we were in between places again — but by September, Josylin rented her first home. Jack was living at the marina, both of us working hard and moving forward.
2024
We celebrated three years together while still living separately — Jack at the marina and Josylin at her house. After a major hurricane caused significant damage at the marina, Jack moved in. That year, he passed all his general contracting exams and began working with Vouler, splitting time between Sarasota and home. We started our first garden and celebrated Josylin’s 21st birthday — a year of growth in every way.
2025
We celebrated four years together and officially made Sarasota home, moving into our current apartment. Josylin left her farm job and began working in veterinary neurology. We celebrated Jack’s 21st birthday and stepped fully into the life we had been building toward.
2026
Five years together — and we got engaged. Now we’re planning our wedding and continuing to build a life filled with adventure, hard work, and choosing each other every day.