how we met
Kristin and I met on Match.com after we had each settled in the DC metro area — she originally from Severna Park, MD, and I from Webster, MA. On our first date, we met at a local pizza shop in Bethesda. Where we quickly learned just how different the two of us are by way of our pizza choices. I only eat pepperoni and she prefers every single topping under the sun to adorn her slice. Lack of shared taste in pizza aside, we did discover that we were true equals later that evening when we migrated to a bar up the street for trivia. Two hours into feeling like trivia hot-shots, we learned that we had only placed 9th out of 12. (Do not underestimate bar trivia regulars.)
how they asked
The story of how I proposed is so much better than our first date. Over the course of several years of dating, Kristin planned all the trips including our first vacation which was a weekend in Charleston, SC — a city that quickly became our favorite destination. To maintain any element of surprise, I had to discretely convince her that we needed to make a late May escape back to the Holy City. We booked our hotel and identified a few restaurants that we wanted to go to — all par for the course. I made all of the preparations including finding a photographer that was willing to help me capture the surprise proposal and arranged for flowers to be waiting at dinner afterwards. Then came the weekend before our trip.
It was a Saturday morning and I had been in contact with a car dealer about a new car that they were frantically searching for — it was finally in! I convinced Kristin to come with me and look at the car that I knew I was going to buy. As we drove to the dealership Kristin glared at me and asked, “Are you sure buying a car is a top priority right now?” It was then that I knew she was ready to have a ring on her finger. I remember trying desperately hard not to smile as I knew it was coming only three days later. It took all of my self-control to calmly reply that I was buying the car I had been searching nearly a year for, and that it was a priority to me above any other life changes. Fast forward to a few days later, we are ready to set off to Charleston on a sunny Wednesday evening in my new car. As we drove, I thought about two things:
1. How irritated she must be thinking that a proposal for her was nowhere in sight, and
2. Exactly what I was going to say when I proposed, replaying it over and over in my head until I was confident I would remember every word.
On a side-note that will be relevant later: We stopped halfway to Charleston to spend the night. As I unloaded the trunk of overnight essentials, Kristin asked me to make sure to bring her orange bag that included shoes, makeup, and jewelry inside the hotel. I panicked and gasped as it hit me. As we were initially packing to leave for the weekend, I remember bringing all the bags down to the garage and setting them behind the car, taking great care to load each one individually into the brand new car trunk. Every bag except for that orange one. I can still see it sitting right where I left it in our garage. Needless to say, the oversight cost me new makeup and new shoes. (At least I would soon be covered on the jewelry front.)
On our first night in Charleston, I remember getting dressed for dinner in the hotel. As we walked out of the room, I muttered “Oops I forgot something,” and ducked back in to grab the ring from where I had hidden it. I had planned to take a casual stroll from the hotel to White Point Garden although Kristin quickly pointed out that we were heading the opposite direction from the restaurant, that she was wearing (new) heels, and that we’d certainly be late for dinner. I ignored her and nervously tried to stall until I knew Aaron and Jillian would be in the park ready to capture our proposal. After about 20 minutes of insisting “I just want to look at the water,” we wound our way through the park to the planned position. Seeing the photographers, I knew it was finally time.
We stopped under one of the large oak trees draped in Spanish moss. I stepped in front of Kristin, grabbed her hands, and began to say what I had rehearsed so many times in my head. “We’ve been together three years now…” — as she cut in to correct me that it had only been 2 ½. It was at that moment I forgot everything I had carefully planned to say and tried to recover. The only thing that came to my mind was, “I’m sorry I forgot your bag with all your shoes, makeup, and jewelry. But maybe I can help you out with one piece that I’ve been saving for the perfect moment.” I pulled out the ring got down on one knee and asked Kristin to marry me.
I remember the “yes” because I was so relieved and could finally relax after holding onto this secret for months. As she cried with excitement and wiped the tears from her eyes, she noticed that people were taking photos of us and immediately missed her makeup products from home again. Thank goodness for Aaron and Jillian who were so patient, kind, and somehow captured beautiful photos as we walked around Charleston in a daze processing the emotions of the day. I’ll never forget that evening and the journey of asking Kristin to be my wife.