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Doug

Wilson

&

Jamie

Gwaltney

Free Union

VA

October 24

2026

The Ring

Jamie’s great-grandmother, Frances Louise Wade, was born in 1916 and married Gerald Ezekiel Miller on May 18, 1935, in Richmond, Virginia. Frances inherited a diamond ring from her godmother Minnie Lee Tally, and its diamond is now the centerpiece of Jamie’s engagement ring.

Luck Tales

Our story starts in April 2024, with a first date that felt a little different from the beginning. The conversation came easily, the chemistry was there—and if we’re being honest, we both had a quiet, suspicious thought: uh oh, this might actually be something. The evidence? The texts. What began as a simple “two truths and a lie” Hinge prompt quickly escalated into Italian translations, elite comedic timing, and an aggressive number of Tom Hanks references: “I said coffee, but I can Colin [Hanks] audible and we could do ‘Ritas [Wilson] instead—whichever makes the biggest Splash (1984) with you.” At that point, expectations were high. Or at the very least: this was not going to be boring. And then… we did what any two rational people with a promising connection would do—we stopped talking for three months. In July 2024, we found our way back to each other. Doug reached out and, to his credit, did not fumble the opportunity. Calm, polite, no notes: “Hey, Jamie! Sorry it took so long to get back to you. If you’re available this week and interested, I’d love to catch up with you!” At the time, Jamie was in California, living her best life and understandably skeptical of a man reappearing after a full fiscal quarter of silence. But somewhere between a couple of gin martinis and a very persuasive hotel bartender, she decided: sure, why not. “Doug! Long time no talk! I’m out of town in CA this week, but I’d be down to grab a drink sometime soon.” Light. Breezy. Noncommittal. A masterclass in keeping expectations low and options open. He was a statistician, after all—he could calculate the odds from here. Two weeks after Jamie got back… nothing. No follow-up. No drink. No closure. But Doug had one final move: a free meal, and just enough self-awareness to include an exit clause. “Hey, Jamie! I’m trying to catch Inside Out 2 this week and wanted to see if you’d like to join. We could do lunch, dinner, or drinks depending on the day—I’m buying. Is there anywhere you’ve been wanting to try but haven’t gotten to yet? Text STOP to ensure this dork doesn’t bother you anymore.” “Oh, I’ve got a million restaurants on my bucket list haha. #1 is Figulina.” Reader, it worked. What was supposed to be a casual catch-up turned into hours of conversation—picking up exactly where we left off, like no time had passed (despite, objectively, time having very much passed). Dinner turned into drinks, drinks turned into closing down the bar, and suddenly it felt a lot less like a second chance and a lot more like… the right timing. And as it turns out, when you know—you really do know.