Southern Belle in Training

Fashion, Travel & Lifestyle Blog || Est. 2012 || Virginia Beach, VA

December 6, 2023

Wedding Wednesday: Our Proposal Story

      It's finally time to recap in the best moment of my life in full detail on the blog! I shared a brief engagement announcement blog post a couple of days after the proposal, but I wanted to have the time to fully write out the full story with all of the little details. This is also the first blog post of my Wedding Wednesday series! I've enjoyed seeing other bloggers do their own versions of Wedding Wednesday series for years and have dreamed about the day when I would be in that life season to document on my own blog!

     This blog post turned out to be quite long! I wanted to include all of the special little details; partly for you to enjoy, and partly for my own memory. But this post truly is special, because Ryan wrote his own side of the story for it! I'll share my version first, and then stay tuned at the end for his.

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Photography by Sarah L. aka The Virginia Concert Photographer

     Ryan and I matched on the dating app Hinge in February 2022, met in person for the first time that March, and then he officially asked me to be his girlfriend on April 24th, 2022. (We were long distance at the time as he was in-progress of moving to Virginia Beach when we met, so he wanted to wait until his April trip to Virginia to make our relationship official in-person.) I wish I could remember the first time that we really discussed marriage and a future together, but it was definitely fairly early on into dating. What I loved about Ryan is that he wasn't afraid to discuss a future together and his forward-thinking intentions, but he also didn't want to rush our dating stage and jump into other life stages too quickly. We were always very much on the same page about dating for at least a year at the bare minimum, but as time went on we seemed in agreement that it could be closer to dating for two years.

     I started ring shopping around our one-year dating anniversary this past spring. (Yes- I did pick out my ring! I will do a separate blog post on that whole story so that this post can stay focused on the proposal. 😀) Ryan did not want to join me himself for ring shopping, but he did encourage me to go either by myself or with a friend. I found the perfect ring at a local jeweler called Adele Diamond in April. Adele Diamond was the fourth jewelry store that I visited. Shortly after finding the ring that I loved, I found out from radio commercials at work that Adele Diamond was having a gigantic sale in July, with discounts as steep as 20-30% on engagement rings. I told Ryan about it. I was like "Even if you aren't ready to propose until a full year from now, still get the ring while it's marked down this much!" He played it very cool when I told him this, and made it sound like it was way too soon to be buying one, good discount or not. So, I honestly didn't think that he took advantage of the sale. But he did! He made the decision to be ready to order my ring in June and officially ordered it in July.

     I had no idea that Ryan had ordered my ring this summer, and as the months of 2023 went on, I truly believed we would be getting engaged in 2024. He gave me absolutely no indications that it would be in 2023. I was worried that I would start to get bummed out if he hadn't proposed by like March 2024. But a big part of me had a feeling that Ryan might wait until our two-year anniversary next April to pop the question. We are taking a big family vacation with his family in March, and I really hoped we would be engaged before that at least. 

     We are supposed to be going to Charlotte, NC in January so that Ryan can finally meet some of my college friends. I was really hoping privately (and also dropping a few hints to him) that I wanted to get engaged during that weekend trip, since Charlotte is such a special place to me. But realistically I was guessing the location would be in Virginia Beach, sometime between February-April 2024. I did always think that our local botanical garden would be a good proposal spot if Ryan chose that! But I always thought it would be springtime if he did the proposal there.


      Now let's get to how our actual proposal came to be! 

      Back in the summer, I received an Instagram DM from a local follower named Sarah. She told me that she was a big fan of my morning radio show and had also started following me on Instagram and reading my blog. Sarah shared that she used to be a full-time wedding photographer but had stepped away and taken up a more traditional 9-5 schedule job in the last couple of years for a more stable lifestyle and schedule. She didn't miss the hustle and bustle of shooting full weddings but did miss being creative with photography and doing smaller shoots. Anyways, she reached out to see if I'd ever be in need of some complimentary professional blog photos to use on here and Instagram. Complimentary professional blog photos? Heck yes!! I thought her message was too good to be true at first and wasn't sure if it was someone scamming me- ha! But Sarah was indeed legit, and her offer stood. Since she is a big country music fan, I also connected her with a manager at the radio station about shooting some concerts for our station, which she started doing in the fall. 

      During our first blog shoot in September, Sarah mentioned that for a future shoot if I ever wanted to bring Ryan and get couples photos instead of solo photos, I was more than welcomed. I told her that was such a kind offer, but that Ryan doesn't like taking photos as much as I do, so I'd probably keep working with her just on my blog. I thought more about it though, and when I bumped into Sarah a couple weeks later when she was shooting a concert for our radio station, I told her I might actually talk to Ryan about doing couples photos in the next month or so. Since we moved in together this year, I wanted a photo of Ryan and I on my Christmas cards this year. I was planning to use a picture from our recent Maine trip, but figured if she was truly offering to do complimentary photos of us, why not use professional photos for our first joint Christmas card if Ryan was on board? 

     I mentioned doing Christmas card photos with Sarah to Ryan sometime in October. To my absolute shock, Ryan seemed very on board! He seemed into it from the get-go which really surprised me, since photos aren't normally his thing. He even suggested doing them at Norfolk Botanical Garden, which is a special spot to both of us. We are members at NBG and enjoy taking walks there once or twice a month throughout the year. I chuckled to myself because I always thought that if Ryan would propose to me in Virginia Beach, it could be likely for it to happen at the botanical garden! (But remember, I was 99% sure I wasn't getting engaged until Spring 2024, so I didn't dwell too much on the fact that he suggested NBG for the Christmas card photos.)

      I set up the photos for the late afternoon on Sunday, November 19th. We already had evening plans with friends for Saturday the 18th, and I didn't want to cancel on our friends to do the photos on Saturday instead. As the month of November began, Ryan started asking a lot of questions about the Christmas card photos. He would repeatedly ask things about what I'd be planning to wear and what time they were happening at. I did think it was interesting that he asked me multiple times for the date and time, which really isn't like him since I typically arrange all of our joint plans! He also wanted to know more about Sarah. How did I meet Sarah? What was her business name? Could he see examples of her past work from when she was a wedding photographer? I thought this was all so interesting since Ryan normally seemed care less about photos. 

     As he would keep asking me questions as this got closer, part of me did start to think "Could Ryan be thinking about proposing? These really seem like questions that he would ask if wanted to propose?" (I told Ryan early on that my one non-negotiable for him popping the question was having professional photographs at our proposal.) But as soon as my brain would go there, I would shut it down for two reasons: 1.) I was still very convinced he would be proposing in 2024 since there was no major indication it would be 2023. And 2.) The larger reason.... who on earth would propose to me on a weeknight as a morning radio host?! Everyone who knows me knows how strict I am about making big weeknight plans since I go to bed early on worknights. If I ever have a work event or a Junior League meeting on a weeknight, you can 100% count on me to be walking out the door and headed home by 7:30pm! Thanksgiving Week is also without fail always one of the busiest workweeks for me in radio, which Ryan is well aware of. I remember thinking to myself that if our photos were on a Saturday instead of Sunday, I'd be a lot more suspicious that Ryan could be proposing! But obviously he would never do something that exciting on what was a worknight for me. So, I honestly didn't dwell too much on these thoughts. 

     The weekend before we got engaged, I was in St. Pete Florida visiting my friend Gentry. I did tell her about all of the questions that Ryan was asking about our Christmas card photos and confessed that my brain had wondered a few times if he was planning to propose that evening. But I also told her that I highly doubted he would propose on a work night, and that every time that my brain went there, I'd shoot it down by remembering our photos were a Sunday evening. 😂 I did tell her though that while I felt ready to be engaged, I was absolutely not expecting it before 2024! And I also shared how I really hoped Ryan would do it when we go to Charlotte, NC in January 2024.

     It was finally Saturday, November 18th. I had just gotten home from the grocery store, when I got a text from my friend Sierra about the plans that we were supposed to have with her and her husband that night. She said they were still getting over a bad cold that they'd had earlier in the week. They wanted to know if we still wanted to do dinner or reschedule. I let Ryan know, and he immediately and firmly said he would prefer to postpone the plans rather than risk getting sick. Typically, I am the bigger germaphobe out of the two of us, so I was a little surprised that he was so adamant to reschedule. (Now it all makes sense! He didn't want to risk us feeling crappy the next day.) Since I had just bought all the groceries to make dinner, I still cooked the meal that I was planning to do for Sierra and her husband. We had a wonderful, quiet dinner at home just us two. We even ended up discussing future dream honeymoon spots at dinner! (But even with that wedding-related discussion topic, I still didn't think he was proposing the next day because the next day would be a worknight with an early bedtime for me!) 

     After dinner on Saturday night, I got really bored and restless. I didn't feel like watching TV with Ryan, but also didn't feel like going anywhere. I then got the most random idea ever for something we could do- painting! I got out a bunch of my old art supplies from my closet. Some of these paints and brushes dated back to my sorority crafting days in college! and Ryan and I started working on individual paintings at our dining room table. We've never done any sort of craft projects before, so this was truly so random. But it was so fun and relaxing. I love that the night before we got engaged was just us enjoying time at home just us in such a creative way. Below is a picture of what we painted. (I bet you can guess which one is his and which two are mine!) 

     On Sunday, we went to church in the morning. We then came home to have lunch and spend a few hours resting and getting ready for the photos. Since I thought Sarah was doing this shoot complimentary for us, I wanted to at least give her a little gift as a thank you. (Note: Ryan did pay her because of course a full proposal shoot is a lot different than just a few complimentary photos for Christmas cards. 😉) I knew that I had some Christmas scented candles in my room somewhere that I keep on hand for gifts. While I was looking for one to give to Sarah, I found a gift that my friend Amanda had given to me a few months ago. Amanda got married in 2020 and had an extra Mrs. themed ring dish that someone had given her, and she had never used. She gave it to me this summer to either give to an engaged friend of mine, or to save it for myself to use someday. I hadn't seen it since the day she gave it to me. I smiled when I found it, but thought to myself "Well, it will still be quite a while before I can use this, since Ryan definitely won't propose until 2024!" It was a foreshadowing sign that I totally missed!

      We headed over to the Norfolk Botanical Garden, and Ryan was acting 100% normal in the car. Nothing about his body language or behavior made me suspect this wasn't just Christmas card photos. We met Sarah in the lobby of the garden. The late afternoon weather was just perfect for Christmas card photos. It was sunny and in the low 60s. One of the first things that I said to Sarah when we arrived is that I specifically did not want the Christmas card photos to have a lot of PDA in them. I literally said "I don't want people on Instagram to see these and send me DMs asking if these are for a special announcement! Just some nice and very tame pictures that I can use as Christmas card photos." Sarah nodded and said absolutely. I have no idea HOW she kept such a good poker face when I said that!! No idea!!! We then spent about 30-40 minutes taking "Christmas card photos" at various parts of the botanical garden.

      Sarah then suggested we move over to the Renaissance Garden at NBG. This is one of the most beautiful spots at the botanical garden. It feels very historical and very Italian, from the landscaping to the style of the large fountain. Had we been doing Christmas card photos on Saturday, we wouldn't have been able to take pictures here because this area is where all of the outdoor weddings at NBG happen, and it's closed to the public almost every Saturday afternoon and evening! But since it was Sunday, it was all ours. Sarah took a few photos of me solo first (to use for an upcoming sponsored Instagram post that I needed some photos of a product for). She then said we would start doing couples photos again but said "First I need to change the ISO on my camera." Ryan then said "What's ISO?", and Sarah explained some basic photography and camera terms to us as we started posing. I later learned this was their code word that it was time for Ryan to propose!! 

      Sarah said she wanted to try something different and had us stand back-to-back. A logical woman might start thinking hmmm... maybe this pose could lead to a proposal when I turn around? But I wasn't in a logical mood, and I was 100% oblivious to what was going on. 😂 I remember thinking that the back-to-back pose seemed weird and definitely wouldn't be what I used for the Christmas cards, but I assumed it was something Sarah wanted for her photography portfolio! Since she was doing these photos for free, I was open to doing any types of poses she wanted if it was something that could help her out. 

     Sarah told Ryan to turn around first. I was still totally oblivious! Then a few seconds later she told me to turn around. And there was Ryan, down on one knee holding the most beautiful ring I've ever seen in my life (the exact ring I fell in love with in April but BIGGER!) and asking me to be his wife. 

      I absolutely blacked out. I truly felt like my soul and brain left my body. I couldn't think, I couldn't speak, I couldn't process. It's a miracle I didn't pass out and was able to keep breathing! I have truly never had a life experience quite like that before of pure and utter shock (the good type of shock that is!). The first thing I wondered is if I was asleep and dreaming, because the timing of this seemed so wild and absurd. There's no way I could be awake right? I never expected Ryan to propose in 2023!! There's no way this could actually be happening right now! After wondering if I was dreaming or not, I saw a giant iPhone calendar emoji flash across my brain that said MARCH 2024 on it. 😂 All I could think about is how this wasn't spring 2024 like I expected it to be! 

    Poor Ryan is still down on his knee for 10-20 seconds and I'm still so much in shock that I haven't even said yes yet! Poor guy! He finally smiled at me and said " will that be a yes?" I was still in too much shock to really talk, but I was able to muster what I hoped was an enthusiastic "YES!" Apparently I also said out loud "But it's not March!" I don't know what my hangup was with the month of March.... but I guess internally March 2024 is truly when I thought I'd be getting engaged? 

      I leaned over finally to kiss Ryan after saying yes, and it was finally then that I had him put on the beautiful ring! I was in awe of how perfect it was. It was the exact ring I had fallen in love with at Adele Diamond back in the spring, but bigger and more beautiful! After the ring was on, I went into shock again, and spent awhile crouched on the ground trying to process the last few minutes! 

      We then took a bunch more photos with Sarah to celebrate being engaged! I will truly treasure these photos for the rest of our lives. I was still in absolute shock!! 

    And lastly, we had to take a special selfie inside of the tropical greenhouse at NBG! We came here for one of our early dates in April 2022, just a few days after Ryan had asked me to be his girlfriend. It was Ryan's first botanical garden trip, and we took a selfie in the greenhouse that ended up being one of the first photos that I ever shared of Ryan online! We had to recreate the selfie with my ring (and Sarah also captured us doing that which was so fun!). 

      Sarah then headed out, but we stayed a bit longer at NBG. We found a bench and that's when we called my parents and a couple of my best friends (some of them who didn't answer their phones for a few hours- ha!). I learned that Ryan had only told my parents and his parents. None of my friends knew about us getting engaged on this day. This is also when I contacted a couple of my coworkers at the radio station with the good news, because I knew I wanted to surprise Cash with the news the next morning. I had them start thinking of a plan for a way for me to share the news in the 8am hour of the show the next day. 

      Then, Ryan had another surprise to tell me about! He had made us dinner reservations at Byrd & Baldwin, which is a very upscale steakhouse in Norfolk, VA. We had never been there before since it is so fancy, and I couldn't believe he took it upon himself to research such nice dining options and find this upscale spot for us to try! We got downtown a few minutes early for dinner, so we walked around outside by the Nauticus ship museum for a bit, and this is when we called Ryan's parents. I also took a ton of selfies and pictures of the ring on my phone. 😊

     Then it was time for our dinner reservation at Byrd & Baldwin. What a fantastic dinner experience! I was so touched that the staff had all signed a congratulatory card for us and offered us complimentary glasses of champagne. The food was all excellent. We had Greek salads, steaks with blue cheese on top, and for dessert I had key lime pie and Ryan had cheesecake. (I wasn't able to get any good photos of the food, but you'll have to take my word that it was great!) This is definitely not a cheap restaurant, but it was certainly a special choice for such a milestone meal. I hope we can return someday for an anniversary or other notable occasion! 

     By the time we got home after dinner, I only had about an hour before bedtime to tell most of my friends and extended family the good news. In an ideal world, I would've been able to keep the news private for a few days and then have the time to call or Facetime the news for a lot more people than I did. But the clock was ticking before bedtime, and I had so many friends that I wanted to invite to listen in to the big announcement on my morning show the next day. So time was of the essence! I quickly texted a ton of friends, promising the full story to come at another time, but in the meantime letting everyone know about what time to listen in to the radio the next day. 

      I finally got into bed around 10pm (way later than normal!), and I think I got about two hours of sleep! I was still in so much shock. I just couldn't get my brain to shut off! (I did crack up watching Delilah sleep so soundly on the edge of my bed through the whole night.) I finally gave up on sleep around 2:30am and decided to just stay awake another hour until it was time to get ready for work. I started responding to texts that had come in late, and I responded to a group text that Ryan was also in. We have separate bedrooms in our apartment, but he was also awake in his room and saw me respond to a text. He came into my room, and we cuddled in bed for about an hour. And just got to talk and relive the joy of the last 12 hours. This might've been my favorite memory after the actual proposal moment itself. He finally went back to his own room to get more sleep when I had to get ready for work.

     Thanks to the help of some of my coworkers, I was able to pull off my plan and surprise Cash with the news on-air! You can see the video of that here!!

       Last thing from me before I turn this over for Ryan's side of the story. I wanted to share my outfit details! My dress was a recent under $20 Walmart find! I had ordered a sweater dress that I had seen a couple other bloggers wear, and I added this black watch plaid dress to my cart as well to try to hit the free shipping minimum. The sweater dress ended up not working out, but I loved the plaid dress! I thought it would be great for Christmas card photos. I have been cracking up that I got engaged in a Walmart dress instead of a Lilly Pulitzer dress like I always imagined. 😂 My over-the-knee boots are a longtime Amazon favorite, and I added some flattering shape to the dress with a Tory Burch belt. My earrings were old Kate Spade. 

     Okay! Time to turn it over to Ryan for his perspective!! 

     I knew I wanted to marry Annaliese well before I made the decision to purchase a ring and plan a proposal. Annaliese and I had an agreement (in the spring of 2023) that she could start “shopping” around at jewelers to figure out what sort of ring she wanted. This way gave me confidence in what I was purchasing was going to be something she loved, but also enough wiggle room to add my own touches to the ring.  

     The ring was purchased in July 2023. I did not get possession of the ring until late August. Since I proposed in late November, there was a lot of time in between to give me a chance to find a great moment to propose. I had a lot of different ideas, some good, some terrible. It even crossed my mind (silly enough) to propose in our kitchen, just so I could get it over with. Not that it was something I didn’t want to do, but the nerves of wanting to propose and starting that next chapter made me so eager I just didn’t want to wait at points. But I’m glad I did because waiting for the right moment was every bit worth it in my opinion. I did consider proposing when Annaliese and I went to visit her hometown in Maine in September. But I knew that trip would be busy with sightseeing and meeting a lot of Annaliese's extended family, so I changed my mind and decided to propose sometime after the Maine trip. (Annaliese here- so glad Ryan didn't propose in Maine! He's right, it ended up being such a busy trip! We barely had time to ourselves.)

     Within that time of having the ring before proposing, the best idea for a proposal in my head that wasn't in Maine was to propose at the local botanical garden. The botanical garden was one of the few spots that we shared time together from the very beginning of our relationship. We are also members of the garden so we can visit as often as we want to, without paying admission each visit. Since I decided that was one of the best ideas to propose, I started to come up with a game plan. The plan was to initiate a date each month for us to go for a walk at the botanical garden. This way, she wouldn’t be as suspicious if I suggested botanical garden as a reason to go there. I was playing the long game. When we would go for walks each month, I’d be curious what her favorite spots were so that way I could find the best available spots to propose when the time was right. This process took almost 3 months alone. I was getting worried that the weather was starting to change, and I needed to find a way to get a photographer set up unbeknownst to her…and fast. I didn't want to propose at the botanical garden in the winter.

     It was such a blessing that Annaliese approached me with the idea of Christmas cards. I knew right away when she suggested we do them with a photographer that it’d be a great idea to suggest the botanical garden as the spot we take them. Sometimes things just fall into place the way they’re intended. In a way, it was a sign that this was the moment that my life story was giving me to start that new chapter.  

      It is truly so surreal to be sharing my proposal story with the love of my life on my blog, after almost a decade of blogging about singleness and dating struggles. I am so thankful to God for the blessing of having Ryan in my life! If you are in a season of feeling very discouraged about dating, please know that I have been there. In fact, I was there for the better part of a decade. If this is you, I'd like to encourage you to read this blog post that I wrote last year! It's all about what steps I took to finally boost my confidence with dating and continue to put myself out there both on dating apps and in-person. I hope it is an encouragement to anyone who is feeling hopeless about modern dating. 


      God Bless,

      xoxo A


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