Gabriella and Connor

How We Met

I have known Gabby my whole life, and I’ve loved her the entire time. In our very first picture together, I think I had just figured out how to walk and she was dragging me around trying to show me something – so not much has changed in the past 24 years. We grew up as family friends: spending vacations together, celebrating major holidays together, and even going so far as to refer to each other as cousins (hence our hashtag #cousinstocaldwells). T

he first time we realized there really was a spark between us was the summer after sophomore year of college. I was studying in London, and she managed to find a job there for the summer so she stayed with me in my dorm room. After classes ended, we took an extra trip to tour Europe, stopping in Barcelona, Paris, Munich, Athens, Mykonos, and Rome. My fondest memory of the whole trip was our second night in Rome. We picked a random restaurant in a random piazza, sat down extremely underdressed and proceeded to have one of the best meals of my life. Three and half hours and quite a few liters of wine later, we were the only people left in the restaurant and we didn’t even notice.

That was when I decided that one day I wanted her to be mine. We went back to our respective colleges after that, and while we stayed in touch and saw each other as much as usual, something was a bit different. Once I graduated, I found a job in the city she was living in and made the jump to move closer to her. And the gamble paid off! One month after I moved, I asked her out on our first official date and the rest is history!

Gabriella's Proposal in Stone Tower Winery, Leesburg, VA

How He Asked

Considering how close our families have been while we were growing up, I knew they had to be involved in the special day. Mind you, I am a terrible liar, so keeping all of this from her was the hardest thing I’ve ever had to do.

I helped coordinate getting everyone to DC (my family from Nashville, her brother from LA, and my grandmother from NYC) to stay with her parents outside of DC. Her best friend is a teacher, so under the ruse of celebrating her last day of summer, we planned to go out to Stone Tower Winery in Leesburg, VA for a double date. What she didn’t know was that I had rented out the upstairs of the winery to hide our family while I took her down to the pond that the house overlooks to pop the question.

When we arrived, her friend texted her saying they would be late, so I asked if she wanted to walk down the pond to kill some time. The one thing I had not prepared for was how unwilling she would be to walk down to the pond. After pretty much begging her to follow me, I finally got her situated in the position I had worked out with her brother (our expert photographer) so that I could propose.

She gave me a kiss and I said “Asking you on that very first date was the second best thing I’ve ever done, behind this” before dropping to a knee to pull out the ring I had hidden in pocket. To be honest, I was so happy I don’t even really remember what happened next except for her saying yes and making me the happiest man in the world.

Gabriella and Connor's Engagement in Stone Tower Winery, Leesburg, VA

Wedding Proposal Ideas in Stone Tower Winery, Leesburg, VA

Then her brother stepped out from behind the bush he was photographing us from and she feared up when the realization hit her. After we hugged her brother, I told her there was another surprise and pointed to the balcony that our family was gathered on, and they began hootin and hollerin like only our family can. We then walked up to the room and took about a million pictures and reveled in the most exciting moment of our lives.

Special Thanks

Nico Greetham | 
Photographer