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Ryan Guard

&

Kylie Mainey

June 23, 2026

Azeitão, Portugal
81 days81 d13 hours13 h13 minutes13 min41 seconds41 s

A Tale of Two Ex-Roommates

Ryan and Kylie both attended the University of Montana. He was a lacrosse-playing junior; she was an incoming freshman, fresh off a gap year in France. They first crossed paths in the dim (dingy?) glow of the Sigma Chi basement during fall semester 2013. Sparks? Maybe. Timing? Terrible - both were in relationships. Over the next two years, they moved through the same circles, shared mutual friends, and even ran into each other on spring break in Seattle - always orbiting close, but never quite colliding. Then came Budapest. Kylie was studying abroad in Prague and joined friends there for a weekend trip; Ryan, freshly graduated and backpacking through Europe, happened to be passing through the same city. He sent a message suggesting they meet up. One spontaneous “sure, why not” later, and everything shifted. After a crashed wedding, a Turkish bathhouse party, and two missed trains, a genuine (and platonic!) friendship took root. Back in Missoula the following year, fate stepped in again. Kylie and her friend, Zoe, needed roommates; Ryan and his friend, Mike - fellow Budapest alum - moved in. The four settled into a little yellow house on Central Avenue, where Ryan and Kylie spent two years as close friends, cheering each other on through life’s ups, downs, and questionable relationship choices. That friendship started to change in the summer of 2017. While working together as butlers at The Resort at Paws Up - and, for the first time, both single - the lines began to blur. A few months later, at a wedding in Mexico, Ryan introduced Kylie as his “ex-roommate,” but quietly told friends, “She’s the girl I’m going to marry.” Still, the idea of ruining a profound friendship held them back from fully committing. And yet, the so-called ex-roommates became frequent fliers. Though Ryan moved to Seattle, and Kylie left for New Orleans to work on a paddleboat off the Mississippi River (seriously), visits between Friday Harbor, Houston and Seattle became frequent. Every goodbye got harder - every reunion got sweeter. Eventually, Kylie moved to California to start her flying career, chasing sunshine and open skies. Two years, countless phone calls, one base transfer, and one conclusive trip to Napa Valley later, they reunited (FINALLY) in Seattle, where love, cats, and a very cozy condo awaited. Ex-roommates no longer, they became partners. Fast-forward to September 9th, 2025 in Naxos, Greece: on a sunrise hike to the summit of Mt. Zeus, with the sun and the moon behind them, Ryan proposed. Kylie screamed “YES!” and the rest, as they say, is history. Seven months later the universe upped the plot twist - after a week of touring wedding venues in Portugal, the couple returned back to Seattle only to find out that they were, in fact … three. Did we mention there’s a baby on the way?! Now, Ryan, Kylie, (and Ryan jr!) can’t wait to celebrate life’s next great adventure with you in Azeitão, Portugal! Vamos comemorar!

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