I’ll start at the beginning. When I was 23, the main diamond fell out of my mother’s engagement ring. My parents searched for it for weeks, but it never turned up. Begrudgingly, they bought a new set of rings, and set the old ones aside. Then, a week or two later, I found a stone on the ground, and asked my mom if it was the missing diamond. Surprisingly, it was. Since they had already bought replacement rings, she decided to save the old ones for me, figuring, “The only reason I have this is because he found it.” I don’t know if she told me about it or not, but I had forgotten if so, because I had no idea.

Last November, I decided I was ready to propose to Naomi. I mentioned it confidentially to my parents, and they told me about the ring my mom had set aside for me. I was so excited, because it was like manna from heaven — I loved the idea of being able to give Naomi a ring with a story behind it, rather than just something bought in a store.

But the rings were yellow gold, and we preferred white gold, so my parents encouraged me to have the stones taken out of these rings and set in new mounts. On December 15, 2012, I dropped the rings off with a jeweler, with some pictures of rings I liked, requesting an estimate for the cost of removing the stones and setting them in mounts similar to the pictures I provided.

The next day, my mother went into a coma due to medical complications. I flew down to PR on December 17, but unfortunately, she passed away that day.

When I returned to Knoxville, I spoke to the jeweler and explained the new context behind these rings. It had already been special that they had been my mother’s, but now that she was gone, the importance was underscored even further.

So while the jeweler started working on the ring, I started thinking about how I wanted the proposal itself to happen. Finding a pretty place and getting down on one knee is well and good, but I really wanted to do something grand and memorable for mine. I’m only doing it once in my life, I want to do it right

There’s a Spanish song called A Dios Le Pido by Juanes that Naomi has always liked hearing me sing along to in the car. So a few months ago I asked my band, Senryu, to learn the song with me. We scheduled secret practices while Naomi was at work, and we learned it over the course of a month or two. So the plan was to play the song at the show, and propose to her in the middle of it.

But I also really wanted to incorporate Gavin in the proposal, because he’s such an important part of my life, and really, I’m asking to marry both of them. But of course, we were playing at a bar (which allowed smoking, no less), so Gavin wasn’t allowed in. But out singer, Wil, is friends with the owner of the bar, so I asked Wil to speak with him on my behalf, and explain the situation. The owner was completely into it. So my plan began to take shape.

First, I spread the word to all of my closest friends, letting them know what I had planned in hopes that they could make it out. In particular, I asked Jeff McClain to be there and bring his nice video camera, because I really wanted some good quality, up-close footage.

Under the guise of having a hard time finding a babysitter on Valentine’s day, I asked Naomi’s sister, Vanya Starr, to drive up from Atlanta and watch Gavin while we went to the show. But secretly, I arranged with Vanya for she and Gavin to head downtown soon after Naomi and I did, armed with a backpack containing a diamond ring and a sheet with two holes cut in it. I then entrusted my friend Kent with the task of coordinating with Vanya to sneak her and Gavin in the back door of the bar while Naomi wasn’t looking.

My band played its set, and then I introduced my song as a Valentine’s day present for Naomi. As we started playing it, Kent snuck back to where Vanya and Gavin were hiding, and brought them up to the area just behind the stage. Vanya then dressed Gavin up as a tiny ghost, and gave him the ring. When I got to the part of the song where I put down my guitar and get off stage, Vanya sent Gavin out to meet me, and I pulled off the sheet to reveal him. He handed me the ring, I got down on one knee, and I asked Naomi to be my companion for life.

To my relief, she said yes We kissed, the crowd cheered, and then I got back on stage to finish the song. Success!

I was incredibly nervous the entire night, and I was amazed that I was able to remember all of the words to the song, and none of my complex machinations went awry. In the end, it went perfectly, and made for a very memorable night.

I absolutely love having Naomi at every show we play. She’s always there for me.

Gavin: “Aw man, I hate Jacks-in-the-Box!”

Way to go with the proper pluralization!

The next morning, I checked the value, excited to see where it sat. Turns out, it immediately plunged down to $640, and then further on down to $610 over the next few days. My $1300 investment of just a few days ago is currently worth around $1220. Woo! Stocks! I’m not good at this.

I know, though, that it’s all in the game, and these little fluctuations are normal, and what’s important is the long-term trend. I’m sure it’ll come back up eventually. But if I could have scripted my first foray into a stock purchase, I would have at least started with some kind of exciting little increase to give you that “Yay I just made ten dollars!” moment, before the inevitable dive bomb. That’s just poor plot development.