Leanne and Derek

How We Met

We met in pre-k 4! I literally get to marry my childhood best friend! We were in the same pre-k class at St. Timothy Parish School, and immediately became friends. During our ten years at St. Timothy we created a really close group of friends. Even our parents became friends, and we all spent our childhood and teenage years going to school together, hanging out at each others’ neighborhoods, and going on group vacations together. Derek was one of my best friends right away, there were zero feelings in the beginning. If you would have asked 15-year-old me if I thought we would ever end up together, I would have immediately shot that idea down.

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He was like a brother. He would tell me his girl problems, and I even talked him through a break-up once. In high school, I attended an all-girls Catholic high school, and he and the rest of our guy friends attended the brother Catholic-all boys school. When it came to Christmas formals, he was always my safe date when I had no one else to ask. I knew we’d have the best time and that it was strictly platonic. When Senior prom was approaching and neither of us had a significant other, we naturally decided to date to each others’ proms. I think my long white dress was definitely foreshadowing.

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That’s when it started. I think we both knew something was there, but for the sake of our friendship, we did nothing about it. We both went away to college two hours away from each other. We remained just as close; he was still my best guy friend. The next four years were spent visiting each other along with all our friends. It was one of those “will they, won’t they” situations with friends betting on how long it would take for us to actually start dating.

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In October of 2016, once we were both back home in Miami, we decided it was finally time to give it shot and try out a real relationship. The best part was that there was no getting to know each other and no introducing each other to family and friends. From the very beginning, it felt like that’s the way it should have always been. It’s felt like a real-life fairytale since then.

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How They Asked

Our relationship began as best friends, so we’re both very open and don’t have many secrets. We had been talking about getting married and getting engaged for about a year, and I knew it would be coming soon. Our friends were so ready for it to happen that it became a running joke to bother Derek about taking too long to do it. I had recently graduated from law school, was almost done studying for the bar exam, and was about to start a new job in a few weeks. Our four-year anniversary was approaching, and my dad was flying in from New York that morning. I of course was very suspicious. I had been very adamant that I did not want a public proposal and really did not want him to do it at a restaurant.

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We had dinner reservations that night, so I knew that if we was going to propose, it would have to be before dinner. The entire day I tried not to get my hopes up, but couldn’t help looking for clues. He was normal as ever and actually had a pretty busy day at work. We got ready for dinner and even had a drink at home before leaving. As we got in the car, I knew it wasn’t going to happen. So I stopped thinking about it and was just really looking forward to a nice dinner on the water. A little background info: Derek often has stomach issues and has to run back inside before leaving somewhere. So that night, right before driving off, he pretended not to feel well. He said he’d be quick, so I waited in the car.

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Not knowing it then, I helped him with his plan when I called him to grab the lipstick I had left inside. He told me he couldn’t find it and was not doing well, and asked me to just go back inside to look for it. When I opened the door, it was total confusion. The lights were dimmed, he was holding sunflowers (my favorite!), playing our song, and my sister was standing in the hallway recording. He managed to completely surprise me. I couldn’t understand where the flowers came from, how my sister managed to sneak in, and how he so expertly faked a stomach attack. The tears started immediately, he got down on one knee, and it was the easiest YES of my life. Our parents and siblings rushed over immediately to celebrate. I’ll always be thankful that he waited until my dad was in Miami to finally propose.

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Our Video

Special Thanks

Alissa Roca
 | Photographer
Alissa Roca
 | Planning