The Proposal

After spending the 2021 holiday meeting each other’s families, we had 2022 to start fresh and take our time. I was 41 and she was about to turn 38 within days. We had talked, and we both wanted kids. She was getting worried about that inevitable clock. Looking back on some of the conversations we had, she wonders why she didn’t scare me off. I tease her occasionally when she brings up those stories. Ok, I tease her nearly all the time. Like how on our second date she was already talking about having kids together. She thinks it took a little more time than that to have that conversation. Maybe she’s right, but it wasn’t much more.

I’d lived nearly 15+ years on my own. She was similar. We’d both had our way of doing things, financials, and our own comforts. We both owned our own homes and had steady jobs. We were set independently. If we were to talk about our future together, we had to figure out how that all would mesh together. For both of our clocks, we needed to know if it was worth spending this time together, or if we should break it off as soon as possible to give each other the best chance of surviving the way we wanted to. There were some uneasy conversations, and I’m sure if this had been 10-15+ years earlier, we both might have said let’s move on to different things. 

I don’t even want to say the word “settled” because that’s not what happened. We realized that nothing that was said was a red flag for either of us. Just being younger would have probably felt like we were pushing into something that we, ourselves weren’t even sure we wanted yet. Everything worked out the way it was meant to happen.

After we got the hard stuff out of the way, she’d started to ask about a ring and engagement. I said that I’d like to date for a year before we think about that. Leanne would then grab me by the shirt, pull me in closer, and growl through her teeth, “Why wait when we both want the same thing?” Maybe I’m miss-remembering this scene because she tells me that’s not exactly how it happened. 

After hearing about a ring and if it would ever happen, I decided to take her ring shopping on Mother’s Day weekend. Not that I had planned it for that weekend, it just happened to be the same weekend I decided that we should go look at rings. She was quite surprised when I told her where we were going. Normally, I’d like to keep the ring a total surprise, but she was so insistent that I wanted her to know that’s what we were doing. But I wanted to try and surprise her somehow.

She tried on quite a few rings. The saleslady was trying to upsell her on a larger stone, but Leanne liked the looks of the smaller one. It was less blingy, and wouldn’t draw attention from the students she teaches. Of course, the saleslady wanted to make a sale and she wanted to make that sale that day. I told her we were just starting to look and wanted to get a feel for pricing. She let us know that the one Leanne liked was a floor model and was the only one left like it. If we want it, buy it soon. We understood and the saleslady excused herself. She came back and asked to speak with me in private. 

We head back to her office, out of view from Leanne. She tells me that they are running a Mother’s Day special and that today is the only day left. Of course, it is. She also mentioned that since this was the display model, and that it had been in the case for a while, the manager agreed to take some more off the price. Alright. She said if I wanted to put a percentage down, I could pay the rest later. Now, I had an idea of what to spend in my mind. This was a few hundred below that. Leanne liked the ring, so I agreed. The saleslady said she’d stay discreet so Leanne wouldn’t know that I had already bought the ring. Good. Maybe I can still surprise her after all.

On our way home Leanne said she really liked that ring and hoped no one else would buy it before us. She also mentioned that she may also like a non-traditional ring and was thinking about going to another jewelry store to look at a sapphire ring. I’m thinking in my head, you can do that, but if you like it more, you’re still getting this one that we just picked out.

The next day after Leanne got off work, she went to another jewelry store to look at sapphire rings. I got a text later saying that she didn’t like it as much and insisted that maybe I should go and buy that one we picked out together.  I asked her if she would like to be surprised or not. Does she want to know that I own this ring? She replied that she didn’t want to be surprised. I took a photo of the receipt and sent it to her.

Now that I have this ring, when am I going to propose? I didn’t have that answer. She already knows that I have it, so is she going to be expecting it all the time? Luckily in June, we were planning our first vacation together. This was going to be the ultimate test. Can we stand each other for hours in the car? We planned to go to Asheville, North Carolina and hit a few places in between on our way to Charleston, South Carolina, where I planned to propose in the most cliché way possible, on the beach.

Since the North and South Carolina vacation was all her idea, I let her plan it out and I would just go along for the ride. Leading up to then, I started taking more selfies and pictures of her and us with my main camera. To make the proposal more memorable later on, I also started to experiment with the built-in settings on my drone—things like auto-circling a subject. My idea was to test these out, but also get Leanne familiar with me doing this so that she wouldn’t suspect anything. I’d launch it from the beach, tell her I was going to do a selfie with the drone, set it on its way, and propose.

Just a day before we left, I was asking her about things to do in Asheville. I had zero knowledge of the city. No idea what was there. This was going to be our first major stop after spending the night at her brother’s place in Lexington. We were planning on 2 overnights in Asheville. She mentioned a trolly tour, an old hotel, and the Biltmore Mansion. I wasn’t familiar, so I had to look up what this mansion looked like. After seeing some photos, I decided to call an audible and change the plan.

We got to Ashville in the afternoon, which left time to explore the city without any real plans. The next day was going to be the first full day. We’d get an early start. We did the trolly tour first I believe. Saw the artist community, the old hotel, the Biltmore village, and heard a lot of history. After getting done, Leanne asked what we should do next. I suggested we do the Biltmore last so that the lighting would be the best it could be for golden hour photos. We went down to the artist community to have lunch and spend some time. 

The entire time I had the ring loose in my pocket. I remember feeling for it every so often. I had also tied a piece of string loose around it as well. It made an easy hoop to stick my finger through and pull out of my pocket. I also did this before I knew about the Biltmore when this was all supposed to go down on the beach. My thought was that if the ring was dropped, the string hoop would make the ring easy to find. I remember sitting down at the BBQ place in the artist community feeling for the ring, thinking, “She hasn’t shown any sign of expecting a ring yet.”

After we finished at the Artist Community, it was starting to get later in the afternoon. I feel like I remember seeing 4 pm on my watch. Leanne asked if we should do something else next, and save the Biltmore for the next day. I said now would be the perfect time, the sun is starting to set. We had already purchased tickets to tour the mansion, and I feel they closed at 5:30 or 6, so we’d be cutting it close. But it didn’t matter, what I wanted to do didn’t need a ticket, and if we missed the tour, we could always go back the next day.

As we arrived, you could tell the popular visiting hours were over. Many parking spots were open. Leanne wondered if we should go straight to the tour. I suggested that we go up the hill overlooking the mansion and get a selfie. I feel that the day had been so busy, and I’d taken so many photos, she was still completely oblivious. 

I start my trek up the hill and find a good spot. I set up the tripod. Leanne was standing under the trees out of the sun. I asked her to go stand out front so that I could get a focus. I think she thought I was just getting a photo of the mansion because she asked, “Am I going to be in the photo?” 

“Yes, we both are.” 

This was not normal though. I hadn’t set up a tripod and taken a selfie with my main camera yet. To make sure I got the photo of the actual proposal, I set the self-timer on the camera. It took a photo every second. I take a deep breath and hit the shutter button to start the recording. I waited a couple of frames so I knew it was working, then I started my walk to her.

As I get beside her, she’s asking how I’m going to take the photo. “Do you have a remote?” I say yes, and start to reach into my left shorts pocket. I feel the string and stick my finger through it, and say, “Are you ready for this?” She responds, “Yeah.”

She was quite shocked (see cover photo). Everything went without a hitch. We were on that hill for what seemed like 10 minutes. We finally made our way down to the tour right as they were closing the line. We made it in, and I saw her checking out the ring throughout our walk through the mansion. We even ran into a couple who said they witnessed the whole thing. Looking at the photos later, you can see them in the lower right during the proposal.

After the tour, we stopped at the gift shop and bought an ornament. Today the string I had around the ring is attached to that ornament.

While sitting in the outdoor food court area, we called all our family to tell them the news. Seemed they all expected what we were about to tell them. 

We spent the rest of the vacation as a newly engaged couple, and I’m really glad I proposed when I did. If I had waited until Charleston, it wouldn’t have been how I expected it to go in my head. We were exhausted from the long days already, and the beach wasn’t what I thought it was going to be. People everywhere. Not a place that was quiet and private. I’m really glad I had looked up the Biltmore and started planning on that being the location. 

This happened in June of 2022, just 10 months after we started dating. Now came the time to plan the date of the wedding. Remember, this is what we both wanted, so why drag it out? Of course, 4 months to plan a wedding is a reasonable time, right? Well, we decided that October 8^th was going to be when the wedding was. This summer will be hectic.