top of page

Our Engagement Story

I know this is long overdue, but better late than never right? Over the summer of 2017 my family, boyfriend JT and I went on a vacation to the Virgin Islands that will forever be the most memorable experience of my life. Keep scrolling to read about the proposal + the ring.

It was the first day of summer, June 21st, and we were on the vacation of a lifetime. We were spending 7 days on a gorgeous catamaran named the Majestic Spirit sailing the Virgin Islands. It was only the second day aboard and let me just say now... I knew I was getting engaged on this trip, I mean it was a perfect opportunity for JT to pop the question and I knew he wasn't going to pass it up. AND after 6 years of dating it was about damn time!! I knew it was going to happen, but I had no idea when, where or how it would happen.

The day before, we spent our first full day at one of my favorite places in the Virgin Islands, Soggy Dollar Bar on Jost Van Dyke in the BVI. I thought for sure he was going to ask me there. I wore my favorite bathing suit, put on a little bit of make up, and made sure my hair wasn't a hot mess...aaaand of course he didn't propose. I was a little annoyed and I thought he blew the best opportunity (I was wrong) He knew I was getting a little antsy so he told me to just wait, that's when I knew it was definitely going to happen soon.

The next morning I woke up and the thought didn't even cross my mind. I put on a random bikini, didn't put any make up on, and threw my hair into a pony tail. After we left Soggy Dollar we began heading to Tortola, another British Virgin Island. I went to sit on the front of the boat to relax while we sailed. The waters were a bit rough so I ended up getting soaked and my hair was a wet, salty mess but I didn't care. We ended up stopping unexpectedly at a random uninhabited island (Sandy Spit) I wasn't sure if we were going to walk on the island or if we were just there so JT could fly his drone around it from the boat. While waiting to hear what the plan was I sat on the front of the boat to get some sun. Little did I know JT, our Captain Dave and his wife Desiree were scheming up a plan for the proposal! Our Captain had taken his dingey over to another catamaran nearby to see if they would help with the plan and they did - they dingey'd over to Sandy Spit and wrote "Will you marry me Lindsay?" in the sand... meanwhile the whole time I was hanging out on the boat clueless!

Finally, we decided that just JT and I would go over to the island and fly his drone around and get some cool pictures and video. I brought my camera and once we got onto the island I started walking around and taking pictures while JT set up his drone and a time lapse on his camera. My whole family was still on the boat but they had a perfect view of us, anchored right off the island. After taking pictures I went over to JT to see what he was up to and he said "Come over here, lets take a picture" and of course I had to say something like "No, take it over here its prettier!" almost ruining his plan! He was flying the drone in front of us setting it up for a picture when he asked me to look at his phone screen where I saw the camera pointed at "Will you marry me Lindsay" in the sand and it took me by complete surprise. He got down on one knee and he was soo nervous he could barely speak. I was so excited and happy I couldn't even tell you what was said after that. All I could do was grab his face and kiss him. It was perfect.

After it happened my mom and dad rushed onto the beach to congratulate us. I was frantic. I knew my hair looked awful, so I tried to throw it up into a cute bun...but as you can see below it just looked like a rats nest LOL it was probably better off in windblown ponytail. That didn't really matter to me though, I was shaking with excitement, I couldn't believe it finally happened!! This was it! The moment I had been dreaming about for months, years even! It was absolutely perfect.

Okay now let's rewind back to 7 months before our engagement.

JT and I were finally starting to talk about getting engaged and I had been looking at ring styles. I was talking to my mom about it and she told me she still had the first diamond ring that my dad gave to her when he proposed over 35 years ago, (she has since upgraded her ring) that's when I knew I wanted her diamond. I loved the idea of having such a sentimental ring, something I can hopefully pass down to my child one day. We took her ring to her local jeweler in Williamsburg, Virginia to see if we could place it into a setting that I liked. Nothing really came of the trip to the jeweler but now JT knew my ring size and had my moms diamond. He ended up taking the diamond to a jeweler in south Florida and bringing a picture I sent him of what I was looking for, and it turned out to be EXACTLY what I wanted. Now enjoy an excessive amount of pictures of it with the Virgin Islands gorgeous scenery in the background and then keep scrolling for the proposal video my amazingly talented fiance created!!!

By the one and only JTC Films!

For more videos check out

Related Posts

See All
bottom of page