I decided early on that I would propose to Caroline outside of Dallas. There were several significant places to choose from, but one stood out above the rest. That location was the wonderful island of Maui.

Caroline’s father has visited the island since he was a child, and he continued the tradition with Caroline. I knew how special Maui was to Caroline when she took me to visit the island over New Year’s Eve, 2019. One trip was all it took for me to understand why they view the island with such fondness.

The perfect opportunity to propose came about when Caroline’s family planned a trip to Maui in May of 2023. As I began to iron out the details, I found out that my parents had an anniversary dinner at the Four Seasons Hotel in Wailea. They described a private dinner with a dedicated waiter and a beautiful view over the beach at sunset. It sounded like it was out of a movie.

Caroline and her parents arrived on the island a few days before me, so I was able to keep my plan under wraps with ease, for the most part. There were no close calls until the day of the proposal. On the day of, Caroline’s brother Sumner saved my bacon when he diverted Caroline who came looking for me at the exact time I was dropping the ring off at the Four Seasons with her parents.

At sunset that night, Caroline and I arrived for dinner and were led through the gardens to our private table. We sat down and talked a bit before our waiter arrived with our “amuse bouche.” Our waiter pulled the cover off the platter to reveal a rose petal covered dish with a ring box in the center. I picked up the box and proceeded to get down on one knee to ask her to marry me!

We had an incredible dinner and followed that up with a surprise celebration with both of our families. For the rest of the trip we got to relax by the beach and enjoy our time as a newly engaged couple.

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