Caroline was never a stranger to the world of dating. After neither high school nor college had yielded the one as it had for her parents and many of the other successful couples she considered to be role models, she had moved to Orlando to start her new adult life fresh, where she could be her own woman and figure out what life might look like without schooling taking up so much of her time and energy. Having salvaged a friendship out of yet another failed relationship, she was fully prepared to be single for a while, focus on herself and her career, when her new friend Kevin invited her to celebrate the end of a stressful week and the homecoming of an old college friend at Player 1, a popular haunt of a video game bar that many of her work friends had raved about. Shaking the hand of a tall, dark-haired, gangly guy whose job training had brought him back into the lives of his college best friends, Caroline found herself instantly fascinated. They talked about video games, comic books, movies, television - they had far more in common than she had expected, and he was such an intelligent conversationalist. On her way home that night, a conversation with her mother from years before popped into her head unbidden. She had asked how her mom had known that Dad had been the right guy, and Mom had responded, "Sometimes, you just know. And I did." Was this what knowing felt like?

As luck would have it, the next time Stephen was in Orlando happened to coincide with Caroline's birthday party, again at Player 1. Though unexpected, his presence was welcome and thoroughly enjoyed, as the crew settled at a gaming emulator cabinet and played everything from Pokemon Snap to Aladdin: The Video Game and many things in between. The two also played Pac-Man and Dig Dug side by side on many occasions that night, a scene that would become commonplace over the next six months. Though she had only known him a few weeks, Stephen had had the forethought and kindness to remember a conversation at their first meeting that Caroline didn't have her own copy of the Infinity Gauntlet comic, an Avengers comic that was the guiding storyline for the Marvel movies that they had bonded over, and gifted his own copy to her for her birthday. This thoughtful and meaningful gift was the first of many ways that Stephen would set himself apart from most guys, and it wasn't long before the two were calling themselves a couple.

On one of their ubiquituous double dates, Stephen, Caroline, Kevin, and Nicole went to go see Inside Out when it was first released in theatres. As is common in Florida, it started pouring down rain while they were standing outside in line for tickets. Stephen offered to stay outside to buy the tickets as the other three ran in, but seeing him getting drenched out there, absolutely miserable, Caroline felt awful having left him by himself. So she went back outside to keep him company, not caring whether she got wet or not. Later on, Stephen would tell her that it was in that moment he knew he loved her.

One particular holiday became very important over the years to Stephen and Caroline, and their whole Ohana, was Dapper Day. A Disney holiday of sorts, Dapper Day is a tradition started in 2011 where Disney and fashion collide as fans across the Disney Parks dress up in formalwear and gallivant through the kingdom or around the world. In October 2017, most of their usual group was going to be absent for Dapper Day, so they decided to make their own! Dressed as Rapunzel and Flynn, the couple and their friends went down to the lake at Epcot, a favorite picture spot, where Stephen used the guise of a photo shoot to surprise Caroline with the ring. They spent the rest of the day celebrating, surrounded by their friends - exactly the way they now hope to spend their wedding.