Kyle was lucky to have access to a friend of Caitlin's family who made jewelry. One thing led to another and this process ending up taking about half a year. With the expectations of proposing during their Spring Break trip, Kyle started to get worried as the ring only arrived the day before their flight to Florida.

Now, the trouble was finding a good time to propose. Caitlin isn't one for a theme park proposal, so the first few days were out. Kyle didn't want to risk the ring being second fiddle to swimming with manatees, so the fourth day wouldn't work either. It was quite clear that a Casey Key beachside proposal was an obvious choice.

Searching through Google Maps, Kyle found the nicest restaurant around that wasn't seafood themed and booked it for Friday evening, their last full night at Casey Key. In preparation for their nicer dinner, Kyle unveiled a new never-seen-before purple polo (Caitlin's favorite color) since he's truly a master of style.

While the dinner was good, the knots in Kyle's stomach remained as he tried to remember his prepared proposal speech. After dinner, the two headed out to the beach at sunset. After finding a good spot to ourselves, Caitlin looked rather expectant. Almost as if she knew that Kyle had told her that he'd gotten the ring... because he had. The prepared speech went out the window, and he mentioned just a few of Caitlin's attributes that he loves so much and popped the question. She said yes! (obviously)