Sheena and Kyle

How We Met

Kyle and I both worked at the same public accounting firm, Ernst & Young, in Chicago. I first noticed him during the busy season in the winter of 2015: this very tall (6’5″), very blonde guy would always walk briskly past my desk without making eye contact with me. This went on for months, from January into the spring, but the cute mystery man never spoke to me (When we later started dating, he told me that he had seen me around the office/in line at the nearby Chipotle and had developed a crush on me, so he had booked a conference room by my desk!).

Kyle was so shy that he only asked me out when we matched on a dating app! We finally had our first date on a gorgeous balmy evening in June at Old Town Pour House in Chicago. We really hit it off immediately and, after we left the bar, the two of us wandered around the city, not wanting the date to end. We moved over to McDonald’s for cones, then a random pizza joint for slices, finally ending up at the beach bordering Lake Michigan, where we shared our first kiss in the twilight against a backdrop of the glittering city lights.

How He Asked

I was very involved in the ring design process, so I knew that a proposal was eventually coming…However, Kyle still managed to surprise me! He had just gotten a new job, and we are huge travel nuts, so we planned an impulsive trip to Naples, FL to see his parents during his week in-between jobs. The second day of our vacation, his parents told us they wanted to take us out to dinner on the beach to celebrate Kyle’s new job. As we were leaving, they told us they’d be taking a different car because they wanted to get drinks with their friends after dinner. And as Kyle and I were pulling out of the garage, he told me he had forgotten his wallet and needed to run back upstairs. He was gone for fifteen minutes, which I thought was a little weird but otherwise didn’t really think anything of it. He had actually gone upstairs to pack our duffels to stay the night at the Ritz Carlton in Naples, and he was really nervous about having to explain why he had our bags with him…He came back to the car, threw our bags in the trunk, got in the driver’s seat, and looked nervously at me ready to offer up an explanation…But I hadn’t even noticed what he’d done! Talk about oblivious haha.

The rest of the ride proceeded with me chattering away and Kyle being unusually quiet. We parked, then began walking along the beach to meet his parents for “dinner”…All of a sudden we reached an isolated stretch of beach and I saw red rose petals arranged in a heart shape, softly-lit lanterns, and champagne set out on a blanket. I turned to look at Kyle and he pulled me to him and told me how much he loved me and that he wanted us to spend the rest of our lives together. I definitely blacked out a little when he kneeled and asked me to be his wife! All I could do was nod while the beachgoers around us cheered! Kyle had worked with the Ritz to plan the proposal, and the planners there had asked people on the beach to take pictures and video so we would have some memories of that day! Everything was so romantic and unexpected, and I couldn’t have asked for a sweeter proposal from a better man.

Special Thanks