How We Met
Shayne and I met in June 2014 on my very first day of work. I was in a finance program while he was in a technology program, both for recent college graduates. Each year, on the first day for the new incoming class of recent grads, both groups attended a welcome lunch. I remember this lunch vividly. I sat diagonally from Shayne who had just finished his first year of work, and I knew that day I needed to know this cute guy. Over the next few months, the flirting began. While we rarely worked directly with each other, we ran into each other often in the cafeteria. A few months go by and I was working on a company project with one of Shayne’s friends in the IT department. Before I knew it, Shayne was somehow getting involved in the project. I later found out this was all a setup and his friend pulled him into the meetings in hopes of him asking me out.
Fast forward to the following summer and that same friend was having a going away party as he was leaving the company. It was the night before I was leaving for an FL vacation and of course, I was no-where near packed. While still being fairly new, I wasn’t sure I would know a lot of people but I did know one thing, Shayne would definitely be there. We spent the night flirting and talking and finally exchanged numbers and promised date as soon as I got back.
A handful of dates later fit in between grad school for me and some very important work softball and basketball leagues (championships) for Shayne, we finally made things official in March 2016. The next three years were filled with so much love and adventure. We traveled to London, Paris, Niagara Falls, Florida, the Bahamas, Banff National Park, multiple cities across Canada, and many many weekend day trips across New England. April 2018 we invited a new furry member of the family, Oliver, and bought a house later that year. I could not have asked for a better partner in crime to spend my life with. Shayne is the most thoughtful, caring, and supportive person and I can’t wait to officially spend the rest of my life with him!
How They Asked
Every year we have planned a trip in March for our anniversary. We had recently planned a trip to Aruba to celebrate 3 years together. I knew this was going to be another amazing trip of adventures and relaxing on the beach and just enjoying being together. Shayne also knew it was going to be amazing but for so much more than that. He had planned this proposal down to every detail. Everyone asked if (or better yet told me) he was going to propose.
I knew he would never try to travel with a diamond ring and so I had zero expectation this would be the moment he proposed, and that worked out in his favor! He thought of everything and could not have done this more perfectly. He hired a photographer to capture the special moment well before we had left and even left a note in his carry on in case security had to search his bag that said: “Please search carefully as there is a SURPRISE engagement ring in this bag!” He truly thought of every little detail.
We had spent our first full day of the trip on the beach pretty much since sunrise. He knew he had the photographer planned to be meeting us at 5:30 before dinner so he knew he had to get me off the beach and ready for dinner well before that. In typical Jess fashion, I made that VERY difficult. I was “parking my butt’ on that beach until at least 5 pm. With a lot of convincing, Shayne finally got me to head back to the room to get ready for dinner so we could “explore” beforehand. 5 o’clock rolls around and we make our way back out to the beach to take a walk before we head to dinner.
Next thing I know, I see a photographer show up. Shayne tells me we were just going to take some nice pictures on the beach. I didn’t even think twice about it since his brother and his now wife did the same thing when they were dating and had photos taken when they were in Jamaica. It wasn’t until he was down on one knee saying,
“I love you and want to spend the rest of my life with you.”
that I knew that was what this was about. After all the tears, and I mean a LOT of tears, I finally screamed YES! We spent the next three days with smiles from ear to ear and couldn’t wait to get home and share the news with all of our loved ones! It was, and forever will be, one of the best days of our lives.