The funny thing is, neither of us know when or how we first met. Shaun was dating one of my close friends in college so we assume we met through her as we we have been Facebook friends for over 10 years. In 2016, we were both single and on Bumble (a popular dating app). I swiped right on Shaun, but Shaun did not swipe right on me. It turns out, Shaun's best friend (Ricky), who was in a relationship at the time and felt deprived of the fun of the dating app game, would frequently swipe under Shaun's profile. He ended up swiping right on me and the match occurred. After matching on the app and recognizing each other, we began catching up and chatting a bit. We made plans to meet up the next Sunday for brunch. Shaun was living in Orlando at the time (a detail he did not share through our texting exchange) and was coming down to Key West for a bachelor party. Sunday comes and goes, and I never heard anything from Shaun. He stood me up. I didn't hear from him until Tuesday with the excuse that he had to go to Orlando and wouldn't be back for a few weeks. A FEW WEEKS? I decided that I did not want to engage further and didn't respond. A month or so passes (Shaun will say it was a couple weeks) and one day, I get a text message from Shaun asking if I want to hang out. Since enough time passed for me to get over him initially standing me up, I said yes. We planned to grab a late lunch at now one of our favorite restaurants, Whisk. From the time we sat down, our conversation took off. We talked for hours about everything and anything. Our first date lasted about five or six hours. We were able to truly connect with each other and found common ground on almost every topic that came up. We learned that we grew up very close to each other, come from very similar backgrounds, had a lot of the same opinions and interests, and were just in sync. I found out later that he called Ricky when we parted ways and told him he swiped right on his wife. And as the saying goes, the rest is history.

My engagement plan involved a bit of deception on my part. I work for a real estate development/investment company which owns luxury hotel properties, so I wanted to surprise Jessica for her birthday (which is in November) with a trip to the Four Seasons in Costa Rica (my company’s property) in December. I had already bought first class tickets and was going to use this trip as the distraction to get her to think that the proposal would take place there. I was planning on waiting to tell her until after the engagement and surprise her with that trip… but a couple of things got in the way. First, when we were going through the design/purchase of the ring, I had to tell her to get sized, so she knew that something was on the horizon. Second, the day the ring was delivered to the house, I stayed home from work, and for some reason (other than being a woman) she decided to check the cameras on the house and saw me walking back inside the house holding the package that the ring came in. She texted me a screenshot and said “what did you get??” But me not knowing if she somehow got a clue as to what it was (she later admitted she had no idea), I felt the need to pivot to tell her about Costa Rica and trigger her brain to think I would be proposing down there instead of any time prior to that. This worked like a charm as her friends began texting me about how excited she was for Costa Rica, given that I was going to propose down there. Now her birthday is in early November and she was planning on spending the weekend with her Mom in West Palm Beach at a family beach condo (about a 90 minute drive north of Miami). So my plan all along was to work with her mom, to surprise her there with the condo decked out in pictures of us, rose pedals, etc. and then we would all go out to dinner after and her family would be there to again further surprise her. After her checking of the cameras incident, I became on edge that I could not raise any suspicion that she would find out about the plan, so I shipped all of the materials for the engagement setup to a friend's house and I would go pick them up on Friday evening after she left with her mom. I then had about 16 hours to complete my design and set-up and transport it to West Palm, where I carved out a 45-60 minute window with her Mom to get access to the unit before they would arrive prior to us heading to dinner. I even rented a car for this, so that if she happened to check the cameras she would think that I was home as my car would be there. During this time, I set the stage and then waited for her arrival in the hallway outside the elevator, holding birthday balloons. The idea was that she is so convinced that Costa Rica is where I would propose, that me surprising her there with birthday balloons would make her think I was simply there as a birthday surprise and the engagement would never cross her mind. This is exactly how it played out… so I then walked her inside the condo and her reaction was priceless. She just started balling her eyes out and saying “oh my gosh” over and over. I walked her through the maze I had created, where the pictures were put up in order from when we first met, to today, so as to walk her through our relationship to that point. After it was over, we then went to dinner at 1000 North in West Palm and the rest of her family was there to surprise her which got another round of heavy tears and emotions.