Jessica and Kyle
How We Met
I was attending my cousin’s rehearsal dinner when family friends of my cousin insisted on setting me up with Kyle. Kyle and his mom are family friends of my aunt, uncle, and cousins and have been for many years – unbeknownst to me! I agreed to the set-up, and Kyle texted me a few weeks later. We kept in touch for about a month before going on our first date in Oklahoma City (where Kyle was living at the time) and the rest is history!
How They Asked
On Friday, July 27, 2018, Kyle and I hopped a plane to meet the rest of my family at our family beach house in Perdido Key, Florida. I was hoping Kyle would be proposing soon, so I had my fingers crossed I would be leaving the beach engaged! My sister and I had arranged for a family dinner one night and bought new dresses for the occasion. Kyle suggested we go to dinner on Sunday night, so I was mentally preparing myself for the proposal during dinner on Sunday. On Saturday afternoon, my sister asked me to help her and her husband take photos of my nephew on the beach.
I threw on athletic clothes, forgot about makeup and let my hair air dry. Kyle came along and we helped entertain my nephew. At 7 p.m., Kyle asked me what that airplane was doing flying over the private beach area. As the plane got closer, I realized it read “Jessica, Will you marry me?” My sister immediately turned towards us and captured the entire moment on camera. My parent and grandparents watched from the boardwalk and walked down to celebrate with us afterward. I would later learn that Kyle and my family began planning the engagement in early July. This will always be my favorite surprise!