Jul 5 2026 | By: Jason Denson
One of my favorite things about photographing Outer Banks family vacations is that you never quite know what the evening has in store. The Dickinson family booked their Outer Banks family photography session expecting updated family portraits with everyone together. What almost no one expected was that the session would end with a surprise proposal!
We met at the Kitty Hawk Pier next to the Hilton for an evening that included 27 family members. Grandma and Grandpa had gathered all five of their children along with their spouses and grandchildren for a week at the beach. Large family sessions like this are always a lot of fun because there is so much laughter, so many personalities, and plenty of opportunities for memorable moments.
The weather couldn't quite decide what it wanted to do. Dark clouds rolled over the Atlantic while soft sunshine filtered through the breaks, giving us dramatic skies that made the beach feel even more beautiful. It turned into one of those classic Outer Banks evenings where every few minutes the light changed just enough to create something new.
After photographing the entire family together, we worked through each individual family, the grandchildren, grandparents, sibling groups, and plenty of combinations in between. With a group this large, organization is everything, but the Dickinson family made my job easy by keeping everyone smiling and ready for the next photo.
Then came the surprise.
Only Grandma, Grandpa, and one of the sisters knew what was about to happen. Everyone else, especially his girlfriend, believed we were simply taking another portrait on the beach. Instead, the youngest son dropped to one knee and completely caught her off guard.
Her reaction was priceless.
The surprise, the excitement, and the tears all happened in a matter of seconds, and being able to document those genuine emotions is exactly why I love moments like these. Watching the rest of the family realize what was happening made the celebration even sweeter. It instantly became more than a family portrait session. It became the beginning of a brand new chapter for two people surrounded by the people they love most.
Congratulations to the happy couple! Thank you to the entire Dickinson family for trusting me to capture not only your Outer Banks family photos, but also one of the biggest moments of your lives. It was an honor to spend the evening with all 27 of you in Kitty Hawk, and I hope these photographs become treasured memories for generations to come.
If you're planning a vacation and looking for Outer Banks family photography in Kitty Hawk, Kill Devil Hills, Nags Head, Duck, Southern Shores, or Corolla, I'd love to help capture your family's story. And if your vacation happens to include a surprise proposal... don't worry, your secret is safe with me.
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