It all started on the slopes of Deep Creek in February 2020, where fate and a questionable black diamond run collided.

Tiffany was on her very first ski trip. Cheered on by her cousins and fueled by a little liquid courage, she decided she was “ready” for a black diamond. Spoiler: she was not. Within seconds she was stranded on the side of the mountain, calling for help.

Doug, there for his annual birthday snowboarding trip, happened upon the cousin of his best friend, stranded, gorgeous, and in need of rescuing.

Having already made a fool of himself earlier that day trying to impress her, Doug quickly came up with a plan. He would guide her down the mountain backwards with Tiffany as his eyes. It sounded smooth in theory, but in reality Tiffany spent most of the ride gazing at the stars instead of pointing out obstacles. Doug collided with her cousin halfway down, but somehow Tiffany still made it safely to the bottom. Not the heroic rescue Doug had pictured, but an unforgettable moment all the same.

They didn’t reconnect until more than a year later, when a bull roast and a weekend with family brought them back together. Doug even drove hours after a hunting trip just to see Tiffany, a gesture she never forgot. A spin-the-bottle card gave him the perfect excuse for a kiss, and a week later they went on their “last first date” in Annapolis. Sushi, Guinness, and a very drunk stranger devouring leftover chicken wings that weren’t his set the tone, and they both knew this was different.

Soon after came a trip to Costa Rica that sealed the deal. Between beaches, mountains, and even a canceled flight that turned into part of the adventure, they realized they had found something special. Tiffany slipped a note into Doug’s bag that read, “I miss you already. –T.” He still has it today.

Back in Maryland, quiet weekends together turned into building a life together. From breakfasts on the porch of Tiffany’s almost-finished house, with Doug cheering her on every step of the way, to that house becoming the home they now share, their story kept growing. When their families met and instantly clicked, it became clear to them both that this was it.

In November 2024, Doug surprised Tiffany with a proposal in St. Michaels, with her best friend secretly helping behind the scenes. What started as a casual day of bar hopping turned into the moment of a lifetime. With their friends and family waiting nearby, Doug dropped to one knee, Tiffany ugly-cried (in the cutest way possible), and said yes.

They have been laughing, adventuring, and falling for each other (sometimes literally) ever since. And if you ask them, it all started with one badly timed black diamond, one very determined snowboard rescue, and one little miracle spin of the bottle.