The year was 2019. It started like any other shift; Kirby reviewed the floor plan for where he would be serving, slammed a taster, and booted up his Toast handheld. Kirby was working at the Double Mountain Brewery on Woodstock and was fully content with being on his own. That’s when Olivia walked through the door to meet her mom and friends for some #DayDrinking. She was wearing a sundress and doc martens and from that moment, Kirby was smitten. As the weeks passed and Olivia continued to frequent Double Mountain, Kirby looked forward to her visits. When Olivia wasn't seated in Kirby's assigned section, he would go out of his way to run drinks over, clean nearby booths (that had already been cleaned), and tried to work up the courage to say something more than “y’all doing okay over here?” Olivia just thought he was doing his job. It would take a few years of this before they would actually go on their first date. In 2022, Olivia had decided to take a new-to-her but tried and true approach to dating: blind dates. Olivia’s mom had continued her weekly meet up with friends at Double Mountain and one fateful afternoon, Kirby’s name was tossed into the ring as a potential suitor for a blind date. When Olivia got Kirby’s number, she suddenly realized she had talked a big talk about blind dates, but was actually quite nervous to go on one. After a few days, she bucked up the courage and sent over a text she had painstakingly crafted — not too formal, not too casual, just the right amount of flirtatious friendliness — and shortly after, they had their first date. What followed has been a beautiful love story; filled with laughter, the realization that their paths had been crossing since 2011, and that it was always meant to work out this way.
There’s an old saying, that “when you know, you know.” And this was no different. Fairly quickly into dating, Olivia and Kirby both realized — they knew — that the other was "the one." Kirby had always envisioned proposing at Rowena Crest, a place from his youth that served as his hideaway to reflect, dream, and get away from it all. He loved the idea of sharing his spot with Olivia and turning it into “their spot.” Olivia, a woman who loves surprises, but also loves being involved, would constantly try and get information from Kirby about the proposal. Like a little kid on the precipice of a birthday or Christmas Eve, she was too excited, she just couldn’t wait! Kirby held fast and did not reveal his cards — he has an incredible poker face. The only detail Olivia could manage to weasel out of Kirby was a simple sentence, “it will be sunny.” On a trip down to Hood River, Kirby put his plan in action. Whether she was subconsciously suspecting or it was by pure chance, right before they hopped in the car, Olivia decided to paint her nails. Once at Rowena Crest, Olivia thought to herself that this spot was one of the most breathtaking landscapes she’d seen. Walking down to the view point, there was a blanket set up with a bottle of champagne on ice. Olivia thought that it was sweet that someone had set that up, but that it wasn’t for her and Kirby. Kirby corrected her, “actually, this is for us. What’s the weather today?” It was sunny! With realization dawning and happy tears prickling at her eyes, Olivia watched as Kirby got down on a knee and popped the question. And of course the answer was, yes, yes, yes!