Jackie and Terrance's Marriage Proposal in St. Augustine

how they asked, Jackie: On a Friday after work, Terrance and I set off on a road trip to visit family (in noticed immediately that they were taking the wrong highway, but ignored my inner “girl gene” and let it go wondering where this weekend would lead. After driving across the state of Florida and starting on I-95, I needed to use the bathroom (I know, way to be such a girl!).

Terrance urged me to hold it for a little while longer. We got off at a St. Augustine exit and stopped at a gas station. When I returned to the car, Terrance was on his phone and said that he had text his roommate from PT school, Todd, to say that we were in the area. Todd said he was in town and asked if I wanted to meet for breakfast. Terrance asked me if I minded stopping for the night. He was feeling a little tired, I am always tired, so we agreed to stop for the night.

Marriage Proposal in St. Augustine

Terrance: Even though the adventure may have started on Friday for Jackie.  The journey started for me when we first met at a young professionals meet up in Tampa about 2 and a half years ago.  The pursuit started for me on that day.  We were bowling and I made every attempt to strike up conversation with her throughout the night, while trying not to over play my hand.

Following that event I did not have contact information for her so I had to do some research and look her up through the meet up group and of course Facebook. I stuck up a playful conversation with her and successfully secured a first date. That first date would grow into something special!!  Which led me to the first part of the proposal process the fun time spent ring shopping which involved my brother and his wife for a little support.  And of course plenty of sneaking around.  All this time eventually led to the purchase of the perfect ring which would later become known as Todd.

After ring was purchased it was time to put the planning into full swing. The planning and preparation went on for a couple of months looking for the perfect opportunity to surprise her. A planned trip home to visit family seemed like a perfect window to make things happen. I reached out to a few proposal planning companies in St. Augustine until I found the perfect person (Stephanie with Eventful Gals) to assist me with making this a truly special occasions and helping to make my envisioned plan come true.

There were plenty of ups and downs through the process; even a moment that it appeared that the proposal would not be successful due to the weekend being full with other events and no room to squeeze another. But it was truly meant to be because a window of opportunity opened and the day was planned with set up and a photographer (Bethany from Bethany Walter Photography) to document the special moment.

So we set off on our journey on Friday after work and stopped well short of the intended destination.  We of course stayed at a hotel that was booked weeks in advance of the interstate to make it believable that it was booked that night, and St. Augustine was chosen because it was a destination with special meaning to us: our first trip together.

Jackie: Saturday morning, we both rose, showered, and prepared to leave the hotel, except Terrance told me I didn’t need to pack my suitcase up; we’d return after breakfast. I thought it was strange, but ignored the girl gene once again. After a detour at Terrance’s PT school, we found ourselves at a cute little café on St. Augustine beach. Terrance encouraged me to get a table while he ordered. I initially went to a two-person table only to remember we were meeting

Todd so I picked a larger table. Halfway through breakfast with no mention of Todd, I inquired as to where Todd was. Terrance asked “why are you worried?” and carried on with his meal. I ignored that pesky girl gene yet again and went along for the ride even though they decided to stay overnight to have breakfast with Todd.

Following breakfast, Terrance headed to historic St. Augustine instead of back to the hotel. We had spent a weekend in March of 2013 there for my birthday. We drove down the familiar streets until Terrance parked. He reminisced that I said she may need a vacation and a HUGE present after the weekend prior and came clean. “We aren’t going to see family,” he explained.

“This is your vacation and present wrapped into one. But don’t worry, you’ll still meet Todd. We’ll

meet him for dinner.” For the next several hours, Terrance and I strolled around the familiar streets and shops in St. Augustine. We stopped to take photos of the bridge, water, and fort (black and white images to be hung in their guest room). I also convinced Terrance to take a string of hysterical selfies throughout the city (which looking back, he too easily agree to). After a delicious limeade, we stopped at the San Sebastian winery in town for a quick wine tasting and purchase “for later” (my ears perked up – what’s later??).

By now, the heaven had opened up and the rain was pouring down. Good thing Terrance had randomly asked me to buy a large golf umbrella before we left. Too bad we had left it in the car. We headed back to the hotel early afternoon. When walking in, I, the unable to relax vacationer, inquired what was next to which Terrance replied “I have work to do” and pulled out his computer. Confused I plopped on the other bed, threw on a movie, and took a nap.

Terrance: Saturday was a fun day with plenty of adventure and exploration and of course plenty mention of my good friend Todd.  It was also a stressful time for me because I had to time things just right and cross my fingers and hope for no rain.  The forecast called for rain that weekend which made me very nervous.  It actually rained earlier that day (we forgot the umbrella in the car).  There was never really a discussion for a backup plan.  Despite all the worries we lucked out with no rain!  We had plenty of fun and coordinated clothing for dinner thanks to Jackie sharing pictures of her clothing options prior to the trip so it was very easy for me to pick out clothing options that coordinated well.

We went to dinner and met the proposal planner at the door in disguise dressed as a waitress at the restaurant that did not take reservations, but she had our table reserved and set up for us. Then dashed over to the beach to set up the final part of the day.  As we finished up dinner I sent a message to the planner to see how much more time she needed, and she said stall for 10 more minutes.  So I used the theme of the weekend and encouraged Jackie to take more selfies.

Jackie: In nicely matching outfits and freshly showered, we headed back out to St. Augustine beach for their 7 o’clock reservation at the Salt Life restaurant. I thought it was odd that Terrance had asked me to go down to the car to turn it on before he joined me, but it is Florida and it was hot. When we approached the restaurant, there was a woman holding the door with two menus. As we approached the door, she asked if we had a reservation. Terrance said yes.

Without stopping at the hostess table (girl gene), the woman led us up the stairs to a two-person table on the rooftop bar. “Where is Todd going to sit?” I wondered, but suppressed that girl gene yet again. We enjoyed the beautiful views of the pier and the ocean, while enjoying a delicious seafood meal. It was comfortable and relaxing; I knew none the wiser that my life was about to change.

Upon leaving the restaurant, Terrance shared that Todd had gotten stuck in traffic, but was close, and asked if I wanted to walk on the beach while they waited. After a quick detour to the volleyball courts to hear about how they just to play there during PT school (I’m wondering why he was telling me this), I was utterly confused of what was going on. Where was Todd? Why were we looking at the volleyball courts? Terrance led me around part of the parking lot and then shared that we could just go out on the beach while they waited for Todd (this Todd guy was really messing up our evening!).

Terrance: After time passed we headed over to the beach to “meet Todd,” but on the way I say Stephanie our planner running through the parking lot?  At that moment I took an unplanned detour towards the volleyball courts and began talking about the days spent during graduate school out playing at these courts.  I kept stalling until I saw Stephanie return.

Jackie: We were no strangers to the St. Augustine pier. We’d stopped here too on our first trip; I insisted on seeing the ocean despite the 40 degrees, lack of appropriate jackets, and incredible wind. We walked out on the pier, where the only others out there were the lonely fishermen who engaged with us and giant pelicans who tried to attack us on more than one occasion. This time, on the sand, Terrance pointed out the couple in front on them getting photographs taken. I hadn’t noticed them. We agreed to walk to the right to get out of the picture for them. Walking under the pier, Terrance pointed out a table in the distance. Yet another thing I wouldn’t have noticed if it weren’t for him pointing it out. We proceeded to walk past it and I swore that the couple and photographer were following us. Terrance stopped and told me he was kidding, the table was actually for us.

Marriage Proposal in St. Augustine

Terrance: We then made our way towards the beach where the proposal was set up.  We walked over and I pretended that it was for the couple out there taking pictures which was actually Stephanie our proposal planner and her boyfriend, and Bethany our photographer.  We slowly walked over to the table and chairs that were set up under the pier.  I pulled out her chair and told her it was set up for us to watch the sunset and we sat for a brief moment.  I quickly realized two things after sitting.  1.  We had a full audience directly above us on the pier and 2.  I needed to get her to stand up again to make my proposal. My only thought was to convince her that we needed to take a selfie to stick with the theme of the weekend to make the moment official.

Marriage Proposal in St. Augustine

After getting her to stand and taking the selfie of course, I grabbed her hand and started to express my love and feelings for her.  I reached into my pocket and pulled out the ring.  (The pocket that I was checking throughout the entire night constantly to make sure I did not lose the ring.) I dropped down to one knee and asked her to spend the rest of her life with me.  I couldn’t wait to place the ring on her finger after she said yes.  We hugged and I kissed and then I thought for a moment she has not even looked at the ring.  I had to make sure she took it all in and liked it because I picked it out without her. I was nervous that she would not like it.

Jackie: As we approached the table, I couldn’t help but to notice the heart outline in the sand, rose pedals, and candles. On the table was sparkling champagne on ice, glasses that I couldn’t help but to notice read “happily ever after.”


Terrance pulled out the chair for me and as I sat down, I noticed of the large crowd that had gathered on the pier.


“Oh I think this is them!” was heard from above. I wasn’t sure what was going on but I told Terrance not to look up. We sat there for a moment until Terrance said “I have a question to ask you.”


He led me by the hand off to the side of the table [apparently we took a selfie which I have a picture of but I don’t remember it. Oops] and began to share that what he was about to ask was forever. He took a ring out of his pocket, got down on one knee, and asked if I would agree to be his wife.

Marriage Proposal in St. Augustine


Ofcourse I agreed, giddy smile and all, and hugged him tightly. The people on the pier and the beach began hooting, hollering, and clapping with my “yes!” Terrance then asked “do you even like it?” as I hadn’t even looked at the ring, which was of course beautiful. I’ll never forget that he told me I couldn’t cry because I’d mess up the pictures. He’s always thinking!

After a few moments, we were greeted by the photographer, who had stopped taking photos of the couple a little bit ago. She congratulated us and asked to take a few cheesy photos with the ring, kissing, and most of all with the pier of people as “they were just as much a part of this. They’ve been here for 45 minutes at least waiting for you!” the photographer shared. Next, the couple who had been photographed when we’d initially entered the beach introduced themselves; the proposal planner and her boyfriend. The proposal planner shared that she had seated us at the restaurant and snuck over to the beach to get everything set up. Terrance had done well! I was in utter disbelief and actually shock; shaking a little even! Planning surprises had always been something we did for one another, but this proposal had seriously outdone itself!

Terrance: After she told me she loved it we sat down and took in some of the sunset and sipped on the sparkling champagne with our happily ever after engraved champagne glasses. We finished the night with a walk down the beach and end to our special day with some ice cream on a warm summer night.  Of course we never got a chance to meet Todd, but things turned out to be pretty special for the two of us!  A lot of planning went into the entire process with plenty of late nights thinking things over and lots of research.  All the time and effort in the end was more than worth it!

Jackie: We settled back in the chairs at the table, where the champagne had been opened and glasses poured.

I made a toast, it was the least I felt I could do after all of the work Terrance had put into this weekend. Then we settled in for some time watching the waves crash in and the somewhat inappropriately dressed beach goers, as Terrance revealed some of the details of his surprise proposal weekend. The light slowly disappeared from the sky and we embarked on the next chapter of their lives. Together. Forever.


And in the end, I did finally meet Todd. Well that’s what I’m calling the ring, that is. :)

Photos by: Bethany Walter Photography