Samantha and Ian

How We Met: Ian and I met on New Years Eve in 2013 n Downtown, Orlando. At the time, I was working as a Web Producer at a local advertising agency and we were on the hunt for a talented Web Developer. Upon meeting Ian, I realized he was a Web Developer and went straight into recruitment mode. Not long after Ian got the job, both of us realized there may be something more there. Our first date was on Ian’s birthday, and we have spent every birthday together since.

How He Asked: I’m not one for surprises. Planning has always been a part of my nature. I’m known for my personalized agenda books, color-coded closet space, and having my activities planned out a year in advance. That’s why when it was time to start talking about marriage with my boyfriend Ian, I just knew I would figure out his plan to propose long before he even had the idea. Or at least I thought so.

Ian and I live in Central Florida, and his mom Bonnie who lives in Ohio was planning on coming down to visit us for two weeks in August. Me being a planner, I thought to myself, “The proposal must be happening while Bonnie is visiting.”

I had myself all convinced, fishing for more information from Ian. Ian knew it was important to me to have family present after he proposed. Having my mom there was a must, so when my mom told me her and my stepdad would be headed up to North Carolina the last weekend of Bonnie’s stay, I was disappointed. She gave me detailed plans of what she was doing in Cashiers, NC that week, and even sent pictures. The proposal obviously wasn’t happening yet.

The last weekend of Bonnie’s visit, we took a mini vacation to Long Boat Key and stayed in one of her good friend’s vacation homes. It was absolutely beautiful. The house was picturesque, placed directly in front of the bay. Even though the proposal wasn’t happening, I thought, “This will do.”

Before dinner that Saturday evening, we got ready and walked downstairs. Ian stepped outside, and I followed, hoping for a nice photo opportunity. After taking a picture together in front of the water, Ian looked nervous. Then, the words starting flowing out like a broken river dam.

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“Will you marry me?”

I couldn’t believe it. It didn’t make sense. Between the “yes, of course!” and the “wait, you’re doing this right now?” I remembered that my family was not there.

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After getting on one knee, and placing the most incredible ring I have ever seen on my left ring finger, I said, “But wait, my mom isn’t here.

To which Ian replied, “Are you sure about that?’

I turned around and watching behind us from the outdoor double doors stood my family, all smiling back at me. My mom and Ian really tricked me! The girl who couldn’t be surprised was now left shocked; a truly amazing feat. We all then went to dinner together, now as a bigger group than I originally expected, and with a much heavier left hand.

A week after we got engaged, we headed to the Turks & Caicos Islands for an “engagement-moon”. This trip was already planned with my dad’s side of the family, but it was the perfect way to celebrate a weekend I would never forget. May the wedding planning commence!