September 18, 2017

Stephen and Amy | San Sebastian Winery Proposal

Two weekends ago, I was blessed to see not one, but two of my dearest friendors get engaged! However, this one hits a little more home. You see, Amy isn’t only one of my friends that I get to work with, but she’s someone that I’ve known for over half of my life! We were the best of friends in high school and after drifting apart for a couple of years after graduation, we reunited and have practically been inseparable ever since. So, it was truly amazing to witness this special moment. Here’s how everything unfolded.

Amy and Stephen have been together for about a year and a half now. Amy is truly herself and comfortable with Stephen and it’s been great seeing them together. He not only brings out the best in her, but challenges her as well. Stephen is such a unique individual, with an infectious personality and really knows how to make people genuinely laugh [and sometimes make them blush] but you can’t help but love him! So when Stephen called to tell me that he was planning to propose to Amy, I wasn’t the least bit surprised! He told me he built her the perfect ring and wanted to show me. I met him at his work one afternoon and got to peek at this ring before she did! It’s gorgeous! He knew that she wanted an Asscher cut diamond and he was actually able to find her one! In my opinion, it’s not a popular cut, so it’s amazing that he was able to get his hands on one! He then had it set in an eternity band. It’s simple in design, but absolutely perfect! A few weeks after seeing this ring and knowing that it would be coming soon [though no date had officially been set] Amy and I had lunch. Somehow after lunch we got to talking about engagement rings and she mentions that Stephen said that he showed one of her closest friends this ring and that that friend approved. I could see it in her eyes that she thought it was me. It was then that I had to take a deep breath and lie, saying that it wasn’t me. All the while I’m thinking “Stephen. How could you say this? Don’t you know that she’s going to ask me and I’m a horrible liar?! Keep calm. Keep calm. Casually lie.” And I lied. And she believed me. Whew! And then we went shopping, crisis averted! Stephen then called me with what we will call Attempt One. He was telling me of this plan of how he would propose at their house while we were there for a get together/styled shoot. I gently mentioned that I didn’t think that was the best idea since there would be a lot going on and because it was deathly hot. I mean, it is August in Florida! After talking it through, he too thought it best to wait and do something more personal and meaningful to their relationship…even though I knew that ring was burning a hole in his pocket! A few weeks later, Stephen calls again. This time he has his whole agenda worked up. He wanted to go Labor Day weekend over to St. Augustine and propose at San Sebastian Winery since it’s one of Amy’s favorite places and it’s the site of on of their first dates! [Cue the “Awwww’s”! So special, right?!] He devised the plan that a group of six of us would go over for the day, but basically as far as Amy was concerned, it was not even his idea. Stephen told Amy that their friends Bridget and Sean had invited them over to St. Augustine for the day to hang out and visit the winery and brewery and a couple of other places as well. She bought it and now we just had to figure out how to get me and Jonny invited. The plan was to nonchalantly ask Amy what they were up to over the weekend and get her to invite us. I wanted to make this happen Friday [which was the day that I was in Orlando] but I couldn’t get it to come up naturally because she kept calling, harassing me to tell her who was getting engaged…which I didn’t by the way! So Saturday morning we chatted again and I asked her what she was up to over the weekend and she went day by day and still never asked if we would be interested even though she knew they were going to a brewery and that my husband brews beer, so when it was my turn I was all like, “yeah, I was wanting to do something with Jonny Sunday for his birthday, but I don’t know what yet” and then boom, I was in. She finally grabbed the bait. Here we were, all things unfolding as planned. The next day, Sunday, we got ready and went over to their house so that we could all ride together. I was quite nervous on how this would play out. I wanted to bring my camera, but couldn’t bring my camera bag, because why would I just randomly do that. So I decided that I would bring my purse. Now, I know this sounds normal to most, but I’ve only been carrying a little clutch for basically the past year. I’ve been over purses even though they’re definitely more convenient, so it made me very nervous that she might just be onto me when I showed up with one. Plus, I’m not sure that anyone else noticed, but my purse to me looked heavy and bulky. But, I carried it like a champ! We started our day out at The Ice Plant and had a drink and snack! Side note: this place is so neat and unique and it has a distillery attached to it, that if you have not been, you should at least check it out. Things were starting to set in for me. I was already nervous the drive over because I didn’t want to give off any vibe that something was about to happen, but now we were just moments away. After the Ice Plant, we walked over to the winery for the real reason why we were here. Being Labor Day weekend, it was super packed up on the terrace where live music was being played, so we went to the other side where it was a little more quiet. At one point, we sent Amy to the other side to look for an open table, and when she left Stephen devised his moment. Amy then sent Stephen and I a text saying that she found a table and for us to come over there. No, Amy, you weren’t supposed to find a table that quickly…so that plan was out the door. Stephen knew that he would now have to wait it out because the music was going and you couldn’t hear anything and there really wasn’t an optimal place to make this happen. That’s what we did. We ordered another pitcher of sangria and a boat load of appetizers for the table and hung out. The guy playing his guitar finally finished his set and packed up and left. This was about the same time that we were about done and ready to go, so our window of time was closing in. Bridget had the idea of having us take a “group photo” up at this crate area where the musician set up. Amy was all about this and I was kind of thinking that at that time that Stephen and Amy would “take a photo” first, but she was all about that group photo. So we all hopped in for one and then back out and Stephen told her that he wanted one of them too. Here it was, go time! As Stephen and Amy sat on crate for their picture together, I casually walked back over to our table and pulled out my camera. He dropped to one knee and I ran back over to capture the moment. It was quick and sweet and all about them. Everyone stopped to watch and gave a cheer as she said “Yes!” The winery even brought them over glasses of champagne! A sigh of relief swept across me as I was finally able to let go of all that nervous energy! Afterward, we finally went over the brewery and shared a flight of beers and told her of all the scheming that had taken place over the past few weeks! I also told her that I was in fact that friend that had seen her ring and she did go back and think it strange that I had carried a purse. I’m just glad that she didn’t have that thought prior and that Jonny didn’t ask me aloud why it was so heavy when I asked him to hold it for a second earlier in the day. We ended our night of celebration together at this interesting little hole in the wall bar called Sarbez, which served the most amazing Grilled Cheeses! They had ones to choose from or you could build your own. I built my own with Gouda, Honey, Green Apples, Bacon on wheat bread. It was ahhhhhmaaaazzziinnnnggg!! Really, you should go there. Immediately.┬áIt ended up being a perfect day with friends!

Amy and Stephen, I am beyond thrilled for you guys! I love you both dearly! I cannot wait for your future and seeing you guys become husband and wife! Wishing you both nothing but the best! Thank you so much, Stephen, for including me in this most special day!!









  1. Katie Wilkerson

    September 18th, 2017 at 5:47 pm

    So beautiful & super excited for Amy ????????????????

  2. Marquette

    September 18th, 2017 at 9:40 pm

    How amazing to get to capture your friend’s proposal!! I love the emotion pouring out of these. I dream of getting to do a proposal someday!

Leave a Reply

Your email address will not be published. Required fields are marked *


Follow me:








The Menu