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Kylie & Jeremy’s Engagement Proposal at Wormsloe

Jeremy is one of the sweetest guys. When we first began talking, I immediately knew he was head over heels in love with Kylie! He planned  the most amazing wedding proposal in one of the most romantic locations in Savannah. I should first explain that Kylie and Jeremy live four hours away in Columbus, GA. Kylie had actually planned a surprise birthday weekend for Jeremy in Savannah, but unbeknownst to her, he found out about her plans! He had been planning to propose anyways and since she was distracted planning for his birthday,  he felt that it would be the perfect opportunity to catch her completely off guard. On the day of the proposal, Jeremy told Kylie that he just wanted to take a quick drive out to Wormsloe to drive to see the  famous live oak promenade. They arrived to Wormsloe and everything went just as planned; everyone is always taking photos there, so Kylie didn’t even suspect a thing when she saw me at the designated propose sight taking photos of the trees! He proposed, and she immediately exclaimed “Yes!”  It was fantastic to be a part of this! Congrats and best wishes!

Wormsloe Proposal

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How did you meet?

Kylie: We met through mutual friends while living in Germany about 3 years ago. Neither one of us was in a place to start a relationship, but we remained friends online and over the phone until we found ourselves back in the states. He was living in Tennessee and I was in Columbus, Georgia. He ended up finding his way to my city while looking for a job. He just came down and never left. Just when it seemed like we were headed in different directions fate brought us to the same spot in the world. We decided to give dating a try and here we are 2 years later!

Where are your home cities?
Jeremy: I grew up in Ripley, TN. Its a small farm town that fames itself for growing the best tomatoes. I grew up in the fields and joined the military when I was 22. I’ve never looked back. I still love going back to see where I began my life and remember how much I’ve grown and achieved.

Kylie: My father was in the military, so I had the privilege of living all over the place, but Columbus, Georgia is where I been the majority of my life and where I consider home.


Jeremy,What made you select the Wormsloe as a location for you engagement session? Kylie loves live oak trees with Spanish Moss. For the last two years, every time she would see one she would say “Baby, look! Those are my favorite trees! Aren’t they SO beautiful?” So when I found out she was surprising me with a trip to Savannah, I remembered the road from the Forrest Gump scene was filmed there. I thought that it would be the perfect place to propose. It was beautiful and secluded. I wanted it to be a private moment that we could share. It had to be something that shed never forget!

Kylie, Where you shocked? I could not have been more blown away. I thought I was planning a surprise weekend getaway for us and for Jeremy’s 33rd birthday. What a thoughtful girlfriend, right? Well little did I know he and my two best friends had been scheming behind my back to make this the proposal city. Neither one of us had ever been to Savannah and I was looking forward to having a new place to consider “ours”. Both being married previously it made it difficult to find vacation spots neither of us had ever been to. I was planning dinner reservations, historic sightings, and even a ghost tour. Jeremy is a lover of history and battle locations given that he is prior military, so when he told me he wanted to check out a historic site I was not at all suspicious. He had gotten me dressed up under the rouse that we had brunch reservations at a pretty fancy place. I love getting dolled up and who doesn’t love brunch? so I did not fight him on that one bit. He said the historic site was en route to brunch and he wanted to go ahead and stop before all the tourists got there and out of convenience of having to come back that direction since we were spending most of our time in downtown Savannah. Again, not suspicious at all. We got to Wormsloe and it is just absolutely stunning. The row of live oaks can only be described as breathtaking. We parked and began walking down the road under the canopy of trees, me assuming we are just exploring the plantation, but he with grander plans. We approached the white picket fence and he began telling me all sorts of sweet things, which is not out of the ordinary, he’s just a sweet guy all the time. When he took my hand and proceeded down on one knee I felt so overwhelmed with emotion. I couldn’t even process what was happening so my natural instinct was to just cry! When I saw he hired a photographer per my specific instructions from our discussion of engagement a long long time ago it made me cry even harder. (I guess he does pay attention to me when I talk about girly stuff!) I hope Nikki was able to salvage anything from the ugly cry face I had to have been doing! I was so overjoyed and I still feel butterflies just telling the story. It was so romantic and spontaneous. It could not have been a more perfect day.

What do you like most about Savannah? How does it compare to other places that you have lived?

Kylie: I love everything about Savannah. I love the beautiful live oak trees, the architecture of the homes, the haunted history, and the not so haunted history. I love the river street scene and all the fun restaurants. I love the carriage rides around the squares and the hilarious tour guide we had on the Old Savannah Tours. I loved the hospitality of all the people and the Pink Lady cocktail at the Olde Pink House. I have live in Georgia most of my life and just 4 hours down the street. I cannot believe it has taken me this long to come down and experience all Savannah has to offer. What I love most about Savannah is this is now our tradition and a new place to make memories for many years to come.

Jeremy: I love the history and architecture of the city. It feels like I’m taking a step back a few hundred years. I am a world traveler. I have seen places that most people only dream about. I have to say that Savannah is the most beautiful city I’ve ever been to. It’s my new favorite place. I see us retiring there when we grow old.

Kylie Raye

AHHHHHH. I love these! there are some great candid moments in there! the colors go so well together! perfect! Thank you so much.

Linda Gaines