Caitlin and Bobby

How We Met

Bobby & I met in August 2015 under an unusual set of circumstances: through mutual friends at a neighborhood gathering. If you’re wondering how this qualifies as being “unusual”, please allow me to clarify: … this was in Sarasota, FL, where the idea of meeting an unfamiliar face is partly inconceivable. For this, when Bobby (a tall, dark, and handsome stranger) caught my eye, I assumed he was a cousin of the host. Bobby swears he noticed me from the moment I walked in and couldn’t look away, though it’s yet to be determined whether my extended proximity to the dessert table was a factor. Following our introduction which occurred from a shared interest of not dancing in public, we spent the rest of the night getting to know one another. I learned Bobby was not a far relative, but an old friend in town for the weekend. The next day he asked for my phone number, we had our first date, and one year later I was ready to join him in Atlanta.

How He Asked

As fans of the classic weekend getaway, Bobby and I started planning our trip to Savannah in early 2017. Though neither of us had ever been, from what I could tell, this southern city encompassed every feature that I love: history, natural beauty, and charm (very original, I know). As Bobby would later tell me, he spent close to a year monitoring the qualities of things that made me light up. Evidently, it was Savannah’s overt abundance of “café lighting” which sealed the deal. This is no joke, as there’s something about being outdoors with “twinkle lights” that puts my heart into overdrive – and he was taking notes. Fast forward to our second night in town, “date night” was planned and ready. In a city known for its scenery and walkability, this story would not be the same without exposing the record high temperatures Savannah experienced during our trip. After refusing his offer to drive and presenting logic that walking would be enjoyable in 101 degrees, I followed an uncharacteristically stoic Bobby downtown.

As we continued, it felt as if the entire city hit pause. Not only did the temperatures magically drop to a cool breeze, but when we approached what would be the proposal location, the sun began to set on the quietest setting I’d seen all day. I remember this moment belonging only to us. Despite an overwhelming sense of calm in the air, I couldn’t help but notice Bobby looked just as nervous as I did. Naturally, I used this as an opportunity to deflect and asked, “Why are you being so weird?” He opened with something perfect along the lines of, “Well, because…there’s something I would like to ask you” … as he got down on his knee. He promises he gave an entire speech, but I lost my composure by then. I became flooded with emotion and not even the “I’m pretending to be sight-seeing” photographer could help me. After a few short lightyears, I remember hearing “I need you to say yes…” as I snapped back to reality and shouted, “Yes of course!” – these were moments that stood to me most, as I also managed to forget to look at the ring until the photographer requested a pose (disclaimer: it was gorgeous).

Engagement Proposal Ideas in Savannah, Georgia

Caitlin and Bobby's Engagement in Savannah, Georgia

Proposal Ideas Savannah, Georgia

While Mackensey snapped away, she made one of the most special remarks I’d ever heard – “Nice to finally meet you Bobby, and you did an amazing job picking out this location!” – Lo and behold, the man who doesn’t have Yelp and leaves a voicemail every time he calls, not only secured an amazing photographer… but secretly drove over 5 hours away to “scout” the perfect spot weeks ahead of time.

We eventually made it to the Olde Pink House where the restaurant had reached capacity with close to 200 guests. This did not prevent staff from providing top-notch service, and our servers made it out to surprise us with dessert and champagne. When we were ready to leave, a woman who did not introduce herself approached our table and said, “I hear you have something to celebrate”. Assuming she was an employee who came to wish us well, we humbly responded, “Yes, we just got engaged!” Our mysterious visitor proceeded to grab the attention of the ENTIRE restaurant by shouting, “She just said YES” and everyone stopped to applaud. Then, in full Broadway style by this one woman-wonder, “Going to the Chapel” (and we’re gonna get marr-ied) was sung for us. It was over as fast as it began, but a public serenade on the night of your engagement is not easily forgotten. We thanked the hostesses for the wonderful experience when they told us they had never seen that woman in the restaurant. Later that night, our photographer posted a first glimpse of the photos. The caption? Savannah is for lovers.

Special Thanks

Mackensey Alexander
Photographer