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Mary Anna

&

Jackson

November 13, 2025

Townsend, TN

Meant to Be (Eventually)

A borrowed bike, a 15-year gap, and one perfect proposal - turns out, timing really is everything!

Jackson and I first met way back in May of 2008 in Oxford, just after I returned from a semester abroad in Ecuador. I went to hang out with one of my best high school friends, Ty Gillespie – and that’s where I met Jackson for the very first time. I remember thinking he was so handsome. We hung out a bit that week before he left for a summer internship in Virginia. We didn’t exchange numbers, but he did let me borrow his bike for the summer. I was so nervous about keeping it safe that I bought a lock from Walmart – partly to protect it… and partly so I’d have an excuse to talk to him again 😉 We reconnected that August when he returned to Ole Miss for his senior year (I was a junior), and we dated on and off that year. We always had the best time together, but after he graduated in 2009, life took us in different directions. Fast forward to June of 2023 – Jackson sent me a follow request on Instagram. I checked with our mutual friend Ty (who confirmed Jackson was single 😄), and once I saw his pictures, I thought, “Wow, he’s still really cute!” I followed him back and sent him a message. We chatted here and there, but things didn’t really take off until August, when we realized we’d both be in Indianapolis the same weekend – Jackson for a college friend’s wedding (shout out to Caitlin and John Rhodes Martin!), and me for a work trip (shout out to my employer Katz, Sapper & Miller!). We met up in Indy and had such a fun time. I figured it was just a one-off hangout… until he called me the next week and we talked on the phone for several hours. If you know Jackson, that’s kind of a rarity 😂 After that long convo, he asked if I’d like to visit Knoxville. I said yes, brought my dog Penny, and we had an amazing weekend. From there, we started seeing each other every other weekend – long distance from Birmingham to Knoxville – and made it work for 9 months. On my birthday in March 2024, Jackson asked if I’d consider moving to Knoxville – and that was all the motivation I needed. I got my house ready for rent in one month, found a place to live in Knoxville, and moved in June 2024. I even got to meet his sweet boys, Patton and Parker, just two weeks before the move. Then, after a year of building our life together in Knoxville, Jackson completely surprised me with the sweetest proposal. He told me we were going to play wiffle ball with his boys and the neighbors (shout out to the Demminks!) – but instead, while I was distracted by our neighbor Blair, Jackson and the boys were setting everything up behind me. When Blair told me to turn around, I saw Jackson, Patton, and Parker each holding a little blue box. Pretty sure my brain short-circuited and I blacked out, because Jackson said it felt like an eternity before I excitedly answered his question with “YES! Of course!!” (to Jackson’s credit, our neighbor recorded the entire proposal and sent us the video, and turns out it took me 21 seconds to respond). The cherry on top was both of his boys also holding a blue box, which they opened to reveal a diamond earring in each. I was speechless. Jackson said he wanted to be able to say all three of them gave me a diamond. It was perfect – and well worth the wait of 38 years. Now we can’t wait to celebrate this next chapter with all of you!

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