diane + connor | candid, fun downtown annapolis engagement

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Name a place and couple more adorable than Diane and Connor in historic, downtown Annapolis… I’ll wait!

On a gorgeous summer night, we explored Annapolis’s main streets together, stopping at my favorite mural (full of wisteria!), State House circle, the city dock and some of the really quaint and adorable side streets.

The colors, the light, the temperature, their outfits, their smiles… all were perfect in their own way!

How they met, in Diane’s words…

“Connor and I met on Bumble on June 1, 2020. We were both looking for serious relationships and our values seemed to align on our profiles. We chatted just a little before Connor asked me to meet up on the following weekend, June 6th. After we made our plans, I didn't hear from Connor for the rest of the week, so I thought that he would forget out plans. I actually ended up making plans for a date with someone else because I thought that he might have ghosted me. Turns out, he had never had any intention of cancelling or ghosting, he was just very busy with paramedic school! He texted me the day before to confirm our date and I cancelled on that other poor sap, lol.”

And how the proposal happened, in Diane’s words…

“Connor proposed on May 15th, 2022 at Early Mountain Winery just outside of Charlottesville. We had a trip planned to Big Meadows Lodge in the Shenandoah for the weekend after and he was planning on proposing that weekend. Connor suddenly lost a good friend from the military in a tragic accident, so we knew that we would be traveling down to Florida to attend the funeral, but we didn't know the exact date. Our trip to Big Meadows was in danger of being canceled, so he had to make an adjustment.

We went to Charlottesville for a friends wedding, and Connor suggested that we stop at a winery on the drive home. He had planned on eating lunch, then going for a walk around the grounds and finding and idyllic spot to propose. While we were sitting at the table, just after ordering our food, he had this weird smile on his face and he looked sort of awkward lol. He then said that he couldn't wait any longer, and pulled out the beautiful ring that we had picked out together from his shirt pocket, which was wrapped in a paper towel! I started crying right away, which made him cry. So he asked me and I, of course, said yes!

Even though we had been trying to be quiet, the waitress overheard and they brought us glasses of celebratory champagne.”

I couldn’t be more excited for your upcoming wedding at the Kent Island Resort this weekend, D+C! You’ve been so thoughtful about every detail and it’s going to be beautiful — mainly because you’re absolutely incredible partners who bring out so much genuine joy in each other.

xoxo,
Naomi