While Kathleen and Ryan did not reconnect until 2019, their story technically spans more than a decade and involves multiple states, close friends and family members, some “dumb luck” or fate, some leaps of faith, and a bit of persistence.

How It All Began (2007-2009)

Ryan quickly befriended Kathleen’s brother, James, in 2005 while Ryan and James were each moving into Farrand Hall to begin their freshman year at the University of Colorado at Boulder. As Ryan and James became close friends that year, James conveniently failed to mention many details about his younger (and much better looking), identical twin sisters.

Over the next 1-2 years, Kathleen and her twin sister, Jennifer, began visiting James in Boulder, and the “secret” was officially out. Jennifer also wound up attending CU Boulder, while Kathleen attended Johnson & Wales University in nearby Denver. Kathleen visited her siblings in Boulder often, so Kathleen and Ryan’s paths crossed from time to time over the years. While today Ryan may unapologetically admit to having a crush on Kathleen during these years in Boulder, at the time he didn’t think that asking his best college friend’s sister on a date was a great way to ensure a lasting friendship with James. Eventually Kathleen moved from Denver to Boca Raton in 2009 to complete her studies at Johnson & Wales’ Miami campus. Kathleen likes to remind Ryan that he failed to attend her going away party, although Ryan’s story is that he never got the invite. The two have agreed that regardless of which is true, it is most likely James’ fault.

The “Lost Years” (2009-2019)

Although Kathleen and Ryan did not stay in touch over the years, Ryan and James remained close friends after college, and they always made a point of keeping in touch, including their annual tradition of traveling somewhere for St. Patrick's Day. Kathleen’s parents and siblings had also relocated to Florida, while Ryan resided in Nashville, TN. By the summer of 2019 James had recently proposed to his now wife, Courtney, and the two of them invited Ryan to come visit them in Cape Coral, FL. Ryan scheduled a long weekend in July to come see what the Southwest Florida lifestyle was all about. During this trip James asked Ryan to be the best man at his upcoming wedding, and Ryan excitedly accepted. Ryan even extended his trip through the rest of the week after realizing (almost) how much SWFL had to offer...but he did not see Kathleen that week.

Reconnecting: 2019

After returning to Nashville from his trip to Florida, Ryan received a message out of the blue from Kathleen. Kathleen told Ryan she heard that James had asked him to be his best man. She asked how Ryan had been and what else was new, and the two began catching up after almost 10 years. Kathleen may tell you that at some point Ryan spent several days ignoring her, but Ryan will tell you he was busy debating the appropriate way for a best man to ask permission from the groom to flirt with the groom’s sister. After receiving James’ approval Ryan and Kathleen started talking on a daily basis.

By the fall of 2019 Ryan was making plans to return to Florida for James’ bachelor party, but he may have been slightly more excited to finally reconnect with Kathleen in person than he was about hosting the bachelor party. James and Courtney had a cake tasting scheduled for family and friends on a Thursday night, but Ryan and Kathleen jumped the gun and met for their first date that afternoon. The two quickly hit it off that weekend, and Kathleen introduced Ryan to her then 2-year-old son, Micah. Micah’s first words to Ryan were “MY Mommy!”

James and Courtney’s wedding was held in Cabo San Lucas, Mexico in November of 2019, and in between their duties as members of the wedding party, Ryan, Kathleen, and Micah got to spend their first full week together. Some may claim the bouquet and garter tosses at James and Courtney’s wedding reception were fixed…but Kathleen caught the bouquet, and Ryan caught the garter.

Even though he had to return to Nashville after the wedding, Ryan realized his heart was already on a different flight...one back to Florida with Kathleen and Micah. Ryan booked a trip to return to Cape Coral for New Years's Eve along with additional trips scheduled for February and March.

2020: A Year We’ll Never Forget

Ryan was scheduled to return to Cape Coral in late March, but when news of the growing COVID-19 pandemic broke, Ryan took the first available flight from Nashville to Fort Myers as the world prepared to face the unknown. What was originally planned as a 1-week trip to Florida turned into two full months, and this gave Kathleen, Micah, and Ryan some unexpected, invaluable time together that could not have happened otherwise.

By May Ryan had to return to Nashville once again as the housing market slowly began to rebound from being sidelined by the COVID-19 pandemic. After a tearful goodbye at the airport in early May, Ryan knew deep down that this would be his last long trip back to Nashville. By July Ryan drove one-way back to Florida to be with Kathleen and Micah, and he had unofficially traded in his cowboy boots for flip flops.

The Proposal: April 30th, 2021

As friends and family members began to increasingly ask questions and make plenty of not so subtle jokes about if and when he might finally propose, Ryan was secretly enjoying the fact that the process of shopping for an engagement ring was already well underway. Kathleen’s brother-in-law, Cliff Burnham, provided Ryan with some cover by inviting Ryan to the driving range that just happened to be in close proximity to the jewelry store, and Cliff provided some valuable insight as the husband of Kathleen’s twin sister, Jennifer.

Kathleen had already planned a weekend getaway for her family members at Disney World, and this created a perfect opportunity for Ryan to pop the question without raising any suspicions from Kathleen. Ryan asked permission from Kathleen’s father, Bill, the Friday before.

Kathleen’s parents, Bill and Margie, traveled to Orlando on Wednesday, and they graciously agreed to be in charge of transporting the engagement ring and scouting potential locations for the proposal. The location would be “Italy” at Epcot, and Friday would be the day. Bill agreed to be the designated ring smuggler for the day, and as the family approached Italy, Bill handed Ryan the ring as Kathleen and Margie walked ahead.

While Kathleen will say in hindsight that certain things were a little different that day, nothing at the time tipped her off, and the proposal successfully came as a complete surprise. The “story” to Kathleen was that all of the family members would get some photos by the lake. As the family prepared to take photos, Micah was not overly interested in posing or standing still. Ryan leaned down and whispered to Micah, “tell Mommy that we have a secret surprise”. Kathleen may have briefly wondered why Ryan remained kneeling on the ground, but it made sense once Ryan opened a box containing the engagement ring and asked Kathleen to be his wife. Kathleen said "Yes!", confirming that Walt Disney World is, in fact, the happiest place on Earth.

A Note From the Couple:

We would like to thank all of our friends and family members for your support and well wishes over these past two years, and we cannot wait to celebrate with each and every one of you! 🥂