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Jacob Rogers

and

Kaylee Ocheltree

June 27, 2026

Canby, OR

How We Met

June 2022 — It all began at Fort Knox, Kentucky. Jacob and I were put in the same squad during Army training. I was making my way down the line introducing myself to everyone. When I got to Jacob he introduced himself to me and I instantly launched into a full ramble about having a friend named Jacob in ROTC and blah blah blah. He smiled and nodded politely, and I remember thinking, “I’m definitely going to annoy the heck out of this kid.” But we became great friends and stayed in touch after training. Fast forward to December 2022. Jacob was at Fort Rucker for flight school, and I was in nursing school, mid–life crisis in full swing. During a catch-up call, I mentioned I needed to get out of Portland. Jacob half-jokingly suggested I visit, and by midnight I had booked flights to Alabama. On New Year’s Day, I landed in Atlanta. We spent the 3.5-hour drive to Enterprise talking nonstop and grabbed a late dinner at Waffle House. From there, everything clicked. We sat on the floor and talked through the night like friends at a sleepover. I had originally planned to stay four days but cut it to three—just in case he was a weirdo(I hadn't seen him since training). But on the last night, neither of us wanted the time to end. We even looked at changing my flight, but it was too expensive. On the way to the airport the next morning, my flight was cancelled, and I could rebook for any day that week. I ended up staying with Jacob for eight days. If not for that twist of fate, we never would have had our Pensacola beach trip—where we held hands for the first time and realized this was something real. The rest, of course, was history. And now, I get to annoy him for the rest of his life :) - Kaylee