We went to high school together, and I always had a crush on Jessica, but thought she was out of my league (she is). Jessica apparently also had a crush on me, but since I never made a move, we went our separate ways in college. It wasn't until the pandemic lockdown almost 15 years later that we reconnected - Jessica sent a late night DM reply to one of my instagram stories about making gumbo. After lots of messages and despite my inability to make a move (still), Jessica gave me her number and we started talking on the phone, sometimes for hours. Talking on a regular basis led to me driving down to Austin, TX (where Jessica lived at the time) to see if our phone chemistry translated to in-person chemistry. After just a little bit of awkwardness (I'll let her tell you about that in person), we knew almost immediately that we had found something special. A couple more visits and only a few months later, Jessica moved to Old Hickory, TN where we have been living ever since!
Since Jessica helps to plan and coordinate most of the things in my life, keeping a secret from her is very hard. So to plan a proposal, I had to use her "rules of engagement" to my benefit. The rules were as follows: 1. No proposal in front of my family if her family is not also present (this is the important one) 2. No proposal on holidays or birthdays Since I wanted some of her family to be present at the proposal (she is VERY family oriented), I had to find a way to invite them without her suspecting anything. I was on a tour that was going to Birmingham, AL, and some of my family had decided to come down to the show. I told her it was the last opportunity for her to see us on the tour, and that I really wanted her there to meet some of my cousins and aunt and uncle. Little did she know, I had invited her sister and sister's fiance to the show, and because of Rule 1, she didn't suspect a proposal. With some help from one of the friends of the artist I was playing for, we were able to corral Jessica backstage for the whole show. On the last song, in front of thousands of people (including my family and hers), I asked her to come out on stage. The audience started screaming, and Jessica looked at me in disbelief - she finally realized what was going on. After proposing, and receiving a "yes," we took some time to talk backstage. Jessica received a photo of the stage via text from her sister, and said, "oh look baby, my sister is at a show too." I told her to look closer, and she realized her sister was at the show, and that I had indeed abided by the "rules of engagement."