Jess thought that she was doing Sarah and I a favor. Just like we had done in Arizona and in Lake Como, Italy in the past, back in July we asked my older brother Tanner and his girlfriend Jess if they could get all dressed up and do a “faux engagement session” with us so we could build our portfolio of engagement sessions outside of Virginia. She had no idea what was really coming… but let’s start at the beginning.

 

Ever since Tanner and I were little kids, our family has traveled to upstate New York at least once a year around the holidays. Our mom grew up in a small town near Poughkeepsie, and we were in that small town this past December to celebrate Christmas as a family. One evening, while out for a drink at a bar, we got talking as a family. Sarah and Jess were on the other side of the bar playing pool, and my Dad nudged Tanner and asked him a question that we had all been wondering. “So, things seem to be going great with Jess. Are you thinking about what’s next? Maybe getting engaged?” Tanner and I had recently talked about this a bit, but even I was surprised by the answer he gave to me and my parents and grandma. Without hesitation, he said, “Definitely. I’m thinking this summer, maybe when we’re all together in the Outer Banks for Beach Week.”

 

We all tried to keep our cool, knowing that Sarah and Jess could glance over at any minute, but with hushed excitement, we started frantically asking questions and making plans. Since Tanner and Jess live across the country in Phoenix, we wanted to take advantage of these times together, especially now that we had a secret mission ahead of us! By the end of that night, it was decided: Tanner would buy a ring sometime in the Spring, then propose when we were all together again for Beach Week. It all seemed so far away, and none of us new that a global pandemic would stand between that night at the bar and the eventual proposal. Before the winter was over, COVID-19 would reach North America, and the proposal fell to the back of everyone’s minds.

 

Then, over Memorial Day Weekend, Sarah and I visited my parents and grandma in Richmond. It was the first time we had seen them since the pandemic had started, so we had a lot of catching up to do. One of the many things we discussed was Tanner and Jess’ engagement, now less than 3 months away. My mom mentioned to us how Tanner had half-jokingly-half-seriously admitted to her how stressed and confused he felt about buying a ring. Should he do it in person? Should he order one online? How would he know if he chose the right one? He had already seen Jess’ “dream ring” on her Pinterest, but he still felt understandably uncertain about making such a big purchase by himself.

 

The next day, Sarah and I looked at each other and almost in unison shared the same exact thought: we should fly out to Phoenix before August so I could go with Tanner to buy a ring. Not because he needed help, but because when I went a picked out Sarah’s engagement ring in Charlottesville, I had my best friend with me. I wanted Tanner to have that same experience. Plus, we were supposed to have flown out to visit and shoot with some of our non-Virginia couples in the Spring, so this gave us an awesome excuse to resurrect that trip, even though we still had reservations about traveling during the pandemic.

 

Less than three weeks later, we were on a plane to Phoenix, Arizona. A few days into our trip, Charlie and Bailey surprised us by also showing up at Tanner and Jess’s new house! They had secretly aligned a work trip with our visit so we could all spend time together in Phoenix, and it made for the perfect plan. Sarah and Bailey took Jess to the mall for a few hours to “help Sarah find some new shoes”, while Charlie and Tanner and I went to a local Jewelry store. Here’s two photos that didn’t make it into our Phoenix + Austin Travel Blog!

 

 

There was a miscommunication between Sarah and I while we were out, and our stories got crossed. Tanner had told Jess that the three of us had gone out to grab a beer, but Sarah thought that our cover story was that we were still waiting for them at the house. The long and short was that Jess ended up upset with Tanner that we had sat around at the house for several hours, didn’t walk the dog, left to get a beer, and expected the girls to go back home and walk him. In reality, we had secretly left the house only a few minutes after them. But Tanner shrugged it off, “She’ll be annoyed for an hour, but it’ll all make sense to her in August!”

 

The rest of our trip went off without incident. Before we left, I casually mentioned to Jess that we’d love to do another faux engagement session with them when we see them at the beach to build our portfolio, then we flew home. The next time we saw them, it was Beach Week. Somehow, all 15 people staying in the house had managed to keep this secret for months, and the day was finally here. My Dad, infamous for his inability to keep a secret, had basically just been avoiding long conversations with Jess since December 😂

 

We started off with the fake-but-actually-secretly-real engagement session photos at the nearby Whalehead Club, a local park with roots that go back almost 100 years, decades before the first beach house was built in Corolla. Tanner and Jess had been through a session like this with us twice before, so with the exception of a few new poses and techniques, it was largely business as usual. Jess was relaxed and joking around with us, happy to help Sarah and I with our business. Tanner was just doing his best to act natural!

 

 

We only spent about 45 minutes there, before Sarah and I had a great idea! “Why don’t we finish the session with a few sunset photos on the dock back at the beach house?” My mom had rented a house for this year’s Beach Week that sat right on the Currituck Sound. We had our own private swimming dock that overlooked the water. So we traveled back to the house and walked back onto the dock. We had Jess put her back to Tanner, telling her that we were preparing her for a pose we do called the “come from behind” where Tanner would grab her from behind in a big embrace. So she turned her back to Tanner, and I gave him the signal.

 

He got down on one knee and pulled out the ring. “Actually Jess, we’re going to do something a bit different. Why don’t you turn around a look at Tanner?”

 

 

Suddenly, it hit her what was really going on.

 

 

We captured more images as they embraced, hugged, and kissed. Jess was still reeling from shock, but we captured just a few more images of them posing for us so they’d have something to send to friends and family. Sarah and Jess embraced — Jess would have a sister for the first time! When we were finished with the photos, we led them off the dock and back towards the house. Standing on the balcony, previously hidden from view by trees, was our entire family and all our friends, cheering on the newly engaged couple!!

 

 

Tanner and Jess,

It’s hard to put into words how excited Sarah and I are for you two. Jess, we first met you at a Sheldon Family Beach Week just a few years ago, and you won over our family right away. Since that week, it’s been such a joy to watch you and Tanner grow closer together and to spend time adventuring with you two in Virginia, North Carolina, New York, Arizona, and even Italy! We couldn’t be more excited to add another member to the Sheldon Family, or for what’s ahead for you two. Tanner, we’re so glad that you’ve found a girl as awesome as Jess to spend your life with, and know that you two have made such an incredible choice in each other. We know that some of the struggles of engaged life and wedding planning are ahead of you, but for now, we hope that these images allow you two to just sit and rest in the joy of your engagement! All that other stuff can come later 😁

 

With LOTS of love,
Hunter + Sarah

 

—

 

If you’re interested in speaking with Sarah and I about your own surprise proposal, click HERE to get in contact with us!

 

If you’d like to view more of our surprise proposals, click HERE to view our portfolio!