Caitlin and Tyler

Wedding Proposal Ideas in Triangle Skydiving Center in Louisburg, NC

How We Met

Tyler and I met “the new way!” We met online, via a cool little app called “Coffee Meets Bagel.” We matched around Christmas time of last year but it took about 3 weeks for us to actually go on our first date. We both live in North Carolina currently but I am originally from Michigan so I was at home with my family to celebrate the holidays. This gave us a great opportunity to chat a lot before meeting for the first time. When we did go on that first date, Tyler picked me up and we went to his favorite Sushi restaurant. I remember thinking we were brave to go eat giant pieces of sushi on the first date! We chatted so long at the restaurant that we didn’t even notice we were the last people there and all of the staff were waiting for us to leave! Our night didn’t quite end there though, we ended up driving around chatting for over an hour longer! I think we both considered the night a success!

how they asked

As told by him – I’ve always known that Caitlin and I have something special: something fun, something exciting, something adventurous. We’re an adventurous couple, so I knew I had to do something different when I proposed. It took me a while to decide on my perfect proposal scenario, but the idea was actually the very first one I came up with – even though I toyed with a few different ideas for a while: skydiving.

I had never been skydiving myself, but it was always on my bucket list of things to do. Caitlin had been for her first dive back in October of 2015 and she absolutely loved it. After her first dive, she purchased an additional dive that had to be used within one year. Why is this relevant to the story you might ask? Because it gave me an inconspicuous way of getting her to go skydiving again without her being suspicious!

After talking to the management at Triangle Skydiving Center in Louisburg, NC, I was convinced that my crazy idea could actually work. We had the logistics planned out for exactly how I was going to get on the ground before Caitlin, how the logistics would work out for the giant heart, and how to get it filmed so we can have the memory forever!

Firstly, I had to get Caitlin’s mom, Cheryl, in on the plot. I wanted to make sure Cheryl was here to celebrate with Caitlin, but Cheryl lives all the way up in Detroit, so we had to come up with a good reason why she would be here, without Caitlin getting overly suspicious. So, we hatched the idea that Cheryl was driving down to vacation at the beach in North Carolina for a week, with a stopover here in Durham to rest for a couple nights. I had also enlisted my parents, my cousin and her husband, and one of Caitlin’s good friends to be in on the plan and make it go off smoothly.

As the day approached, I also decided to hire Elijah from Morgan Scott Films to capture the whole day in glorious 4K so we could all cherish it forever. In order to keep Caitlin on her heels, we hatched the idea that Elijah was there filming a new marketing video for the Skydiving Center.

Once the day arrived, everything started off incredibly smoothly. We walk in the door, get checked in, then, the owner walks up and asks if we wouldn’t mind being filmed for their new “commercial.” Of course, we both agreed! Elijah began “interviewing” us both to ask about our experience with skydiving and how we were feeling about the adrenaline rush ahead. As part of the video, Elijah also placed microphones on us to record for the actual jump – what a great plan!

As the jump time came nearer, our gaggle of accomplices were holed up in another building at the small airport awaiting our signal to run out and begin their plans for laying out a giant heart on the ground that I would be waiting for Caitlin in. Our only hitch in the entire day came from the plane being delayed by nearly three hours for maintenance. But, what better time to have a plane that might not be airworthy than when we’re about to jump out of one?!

Finally, it was time for the jump! Caitlin and I are both still novices, so we were strapped into tandem instructors for the jump. Of course, both our instructors were in on the plan, so they knew how important timing was for me to be on the ground first, have time to change out of my jump suit into my jacket and jeans, then be waiting for Caitlin to land while I had a bouquet of flowers and ring in hand.

Incredibly, there wasn’t a single nerve in my body that was fearful or scared. I can honestly say that the plane ride up was one of the only times in my life that I think I’ve experienced pure bliss. Looking out the window as we climbed higher by the second, all I could think about was how happy Caitlin was about to (hopefully) make me by agreeing to become my wife. I wish there had been more filming in the plane before we jumped, because I don’t think a single second ticked by that I didn’t have the biggest grin slapped across my face.

I was the first to jump out of the plane at an altitude of 13,500 feet. Whereas most jumps consist of around 60 seconds of freefall, mine was nearly 100 seconds. In order to help me get on the ground in time to set everything up, we needed to plummet towards earth longer at 120mph than anyone else on the plane. Once the parachute opened up around 5,000 feet, it was a much quicker descent than I expected! We made some amazing aerial turns that had us on the ground in no time.

As soon as we hit the ground, the staff came running over to get me unharnessed and help me to my feet. As I ran over to our awaiting family and friends, I was literally stripping off my jump suit and grabbing for my suit jacket, flowers, and, of course, the ring! It was only about two minutes after I hit the ground that Caitlin was about to land. Being the incredibly observant girl that she is, she already knew what was about to happen from nearly 6,000 feet in the air. She spotted the giant red heart laid out on the ground and her heart nearly stopped.

Once she landed, she took off for me in a scene that I will never, ever forget for as long as I live. Smiling, half crying, half walking, half jogging, she ran into my arms. After embracing her for a moment, I dropped to my knee and pulled out the ring.


As told by her – Last year I went skydiving for the first time and absolutely LOVED it! I love it so much so that I bought another half price dive! The 1 year expiration date was quickly approaching so I asked Tyler if we could go together, him for his first dive. He happily agreed and as he normally does, he took charge of planning the entire day. I was very much looking forward to it! My mom and her boyfriend were in town from Michigan because they were on their way to the beach for a vacation (or so I thought).

The night before our dive, we had a great dinner with them and because my mom thinks we are crazy to even think about jumping out of a plane, she decided she did not want to watch us dive. I thought nothing of it, as she was NOT happy the first time I went skydiving. That day was filled with excitement and nerves! We arrived at the skydiving center and was promptly greeted by a young guy with a video camera. He explained that he was shooting a promotional video for the skydiving center and even had the entire staff on it. The front desk girl and the owner of the entire skydiving center were talking with him, pointing him in different directions to shoot this, shoot that. I was *slightly* suspicious at first but the fact that the entire team was talking with him it put my thoughts to rest. It was finally our time to jump and off we went!

My guide and I jumped out at 12,500 feet and free-fell for approximately 60 seconds before pulling the parachute cord. It was a crisp autumn day with perfect blue skies, so the float downward was breathtaking, and breathtaking it was. My guide tapped my shoulder when we were at about 6,000 feet and pointed towards the ground. The simple question “what’s that” was all it took for me to about lose my mind! On the ground I saw a giant red heart near our landing spot back at the airport. I instantly knew what Mr. Tyler was up to and the only thing I could do was scream, smile and kick my little legs. It felt like an eternity later but when we finally landed I saw Tyler standing there in the middle of the heart wearing a suit jacket and holding flowers. I ran as quickly as I could while wearing that giant suit and harness and threw my arms around Tyler. He asked and I obviously said YES!!!!

I hadn’t even realized that my mom and Mark, both of Tyler’s parents, his cousin and husband and my best friend Leslie were all standing around us until everybody rushed forward full of hugs and kisses! They were the ones that set up the heart after waiting for a few hours hiding in the parking lot. This was also where I learned that my friends and family are good little liars!!! Mom and Mark weren’t actually going to the beach, they came down to celebrate our special day. Elijah, the videographer, was there for us, Tyler had hired him to capture every moment of our engagement and the entire team played along with it! It was, as I like to call it, the best day *yet* as I know I have many many more amazing days with this perfect man!!

Our Video

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Special Thanks

CMB (do insta @coffeemeetsbagel)
We met on the app Coffee Meets Bagel!!