Jenna and Dan

Image 1 of Jenna and Dan

How We Met

After many failed attempts at relationships, we both started to lose faith in the dating world, so we downloaded Bumble. I messaged Dan, and he responded right away. I quickly found out that he attended middle school at the same school that I, now 14 years later, teach at. We realized that we knew some of the same people, and my coworkers even began telling me memories they had of Dan in middle school. Even though most of the stories involved him causing trouble in class, I still decided to go meet him for a date. He wanted to take me to a nice dinner in uptown Charlotte, but me being nervous, changed the plan last minute and asked him to meet me at a local bar instead. I made my friend, Alex, tag along so she could ease my nerves (and lets be real, we had to make sure he was normal). By the time Dan got there, we were already drinking our second beer and enjoying a plate of nachos, and the world got a little smaller once again – Alex went to school with Dan’s brother, and Dan went to school with Alex’s sister. Keep in mind, most people aren’t from Charlotte. It’s a transplant city. Dan is one of the very few born in Charlotte, so it’s rare to find someone with all of these crazy connections. Dan seemed like a good guy, so Alex left and we enjoyed our first date. At one point, a guy dropped his glass and it ended up cutting his arm. Blood was gushing everywhere, and Dan ran over to help him put pressure on the cut and clean up the glass. The guy ended up having to go to the emergency room, but watching Dan spring into action was the first time I realized just how amazing he really is. We continued going on dates for the next few months, but nothing was official. We both knew we liked each other a lot, but everything was really casual. Three months after our first date, we went to dinner, and something changed. I got to the restaurant before Dan, and he saw me as he walked in. He realized at that moment that he was ready to fully commit to me. Over a delicious sushi dinner, Dan confessed all of his feelings and fears, and I did the same. We talked about how we were ready to give it a shot, because even if we were scared, it felt too good to not try. After that moment where each of us let our guard down, things started to go really fast. We had only been officially dating for two weeks, and Dan tagged along on my family’s vacation to Mexico. It seems crazy looking back on it, but in the moment, we knew how much we cared about each other and it just seemed right. When we returned to Charlotte after our incredible vacation, we became inseparable and haven’t looked back since!

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Image 3 of Jenna and Dan

how they asked

Dan works for an insurance carrier in Charlotte. As a part of his job, he has to attend a lot of business dinners with agents from other companies. About a month ago, Dan forwarded me an email from Meg, the Regional Vice President of his company. She said that on Friday, August 4th, there was a cocktail hour and dinner planned at a restaurant in uptown Charlotte. She explained all the details and who would be there, and told him to invite me. She specifically added that this wouldn’t be intimidating, and I couldn’t say no this time because everyone’s significant others would be there as well. I was invited to a dinner once before but I didn’t go, so this seemed completely believable to me.

The dinner came up in conversation a few times over the course of the next month, but I never thought anything of it – other than the fact that I was nervous to go to a business dinner with so many important people. Dan bought me a dress to wear, which also didn’t raise any red flags because he’s known for surprising me with new clothes (he has better fashion sense than I do). On the day of the proposal, we were driving uptown and Dan told me he was going to call the Meg to see if she was at the restaurant yet. She said that her and her husband were killing time in Romare Bearden Park, a beautiful park in the middle of the city, and to join them there. The park is right next to the restaurant, so it made sense.

It turns out that Dan was actually talking to our photographer, Megan, who was waiting in the park to take pictures of our special moment. As we were walking through the park to find Dan’s boss, he stopped and pulled me in for a hug. He does that all the time, so once again, I didn’t think anything of it. He held onto me for a minute and kissed my forehead over and over, until he pulled away and said “I have a confession. Meg…isn’t here. And Steven, he isn’t coming. There’s no dinner. It’s just me and you, and that’s all I want forever. I hope you know how much I love you.” He dropped down on his knee and asked me to marry him. I was in complete shock and immediately started crying before I could even say yes!

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After the proposal, Megan took pictures of us around Romare Bearden Park. Then, Dan had a night filled with surprises planned, including a stay at a nice hotel in the city and dinner reservations. On Saturday morning, the surprises continued when I walked into the restaurant we had our first breakfast date at, and I saw my mom, who lives in Vermont, sitting at the table. The rest of the weekend was filled with amazing surprises that Dan thoughtfully planned. I’ve never been more surprised! It was the most perfect weekend.

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Special Thanks

Megan Quackenbush
 | Photographer