On August 26, 2014 Katy started her new job at Insightly, and was quickly seated directly across from "Dreamboat Dan". With a ton of help from their determined matchmaker Nora, along with many billable hours spent flirting in the office, Katy and Dan soon found themselves sneaking off to take lunchtime walks along the water. On March 20, 2015 Dan took Katy on their first date. Because it was her half birthday, he surprised her with a big slice of tiramisu & a birthday candle. They've celebrated the day together every year since.

On Christmas day 2019, Katy opened her gift from Dan to find a note saying they were leaving for The Grand Canyon in 2 days - a place she'd been pestering him to visit since before their first date. They were up before dawn on December 28, 2019 to watch the sunrise over the canyon, and then embarked on the Rim Trail. On the way back, Dan asked two friendly ladies to take one last picture, and handed them his phone and Katy's camera. Katy struck a pose, smiling for the picture, and it was at that moment that Dan dropped to one knee.