How We Met: Jessica and I met playing rugby at Smith College (yes, this is a true story). She was a witty sophomore with lots of friends and I was a first-year trying really hard to be cool. The short version of a long and embarrassing story is that we started dating not long after we met. We were together all through college, including time living apart in different cities, a semester I spent in Mexico and Jessica’s first year of Teach for America in New Orleans. After a year-long breakup in 2013, we got back together last year and Jessica decided to move to Columbus, OH to be with me.
How They Asked: I work in communications. I usually know exactly what to say, how to say it, and can speak in front of people without being nervous. But proposing was easily the most difficult speaking assignment I’ve ever had.
By the time I proposed, Jessica and I had been dating for nearly six years. When she moved to Columbus, we started talking about getting married, and by the time the holidays came around, we had already seen an amazing engagement ring that I secretly bought without telling her.
Even though Jessica knew I was planning to propose, she didn’t know when or how. After finding the perfect ring, I kept her waiting for several months while I came up with a plan and talked with both of our parents. I finally decided it was time to pop the question just a few weeks before we were scheduled to see her entire family for their annual Passover gathering.
My plan wasn’t very complicated. I wanted to propose at Franklin Park Conservatory, a beautiful botanical garden in Columbus which was starting their annual butterfly exhibition on the weekend I had in mind. I also hired a photographer, Amy, to hide and secretly take pictures of the whole thing.
For as simple as my plan was, it felt like almost everything went wrong.
The morning of the proposal, I woke up feeling anxious but eager to spend a relaxing day together doing all of Jessica’s favorite things. Instead, she woke up before me and had already invited a few friends out to brunch, not knowing they were all planning to have a small surprise party for her later that day. We had a great time, and they did an amazing job of playing dumb about my plans.
Thinking I was now in the clear, Jessica and I decided to hang out at our house for a few hours before heading over to the Conservatory. When we got home, she promptly fell asleep. I was actually relieved not to have to hide my nervousness for a few hours, but she overslept and then had a really hard time getting ready. We ran late – really late – meanwhile Amy was desperately trying to corral crowds of people and keep the area clear at my perfect proposal spot.
When we finally got to the Conservatory, Jessica asked if we could make a bathroom stop and, being super smooth and relaxed at this point, I said no. Instead, we quickly made our way to the spot that Amy and I had pre-selected. I could tell that Jessica knew something was up, and I was so distracted by just how many people were around that I almost couldn’t get the words out. Somehow, though, I did manage to get down on one knee and ask Jessica to marry me with a few well-chosen words that brought tears to both our eyes.
Most importantly, she said yes.
Hiring a photographer was a great decision. We now have that moment captured forever and it looks way more graceful than it felt at the time.
During that whole day, I kept feeling like nothing was going the way I had planned. And in a way, I was right. But the only part of the day that actually mattered was that Jessica said yes, and that went exactly as I had hoped.
Photos by Amy Ann Photography