Kaitlyn and Robert met in the closing days of a beautiful summer, in August, 2019. As many couples in their generation have, they met through an online-dating app. They shared their first date in idyllic, downtown Issaquah at one of Kaitlyn's favorite hang outs, the Rogue Brewery Pub. After a bite to eat, Kaitlyn showed Robert around the area. They had a lot to say to each other the entire date; which probably surprises no one who knows these two chatterboxes. Robert liked the surfer-girl vibe that Kaitlyn was giving off, her having just returned from a paddle-board trip. Soon after they made plans to go paddle boarding, and they cruised off into the sunset together.

Fast forward to about a year and a half later; Robert was standing in the back yard of his and Kaitlyn's home on Camano Island. Robert and his dad Kevin had just finished building a brand new deck. Kevin asked Robert if he was thinking about proposing. The groom-to-be had already known where he was proposing for quite some time. He told his dad to keep it secret, but that an upcoming, second trip to Hawaii would be the perfect occasion for their engagement. Robert and Kaitlyn returned to the site of their favorite trip together, Oahu, for a long stay in paradise in September 2021. After returning from a catamaran cruise, the couple walked to a spot under a Kamani tree that stood seaside, near the lagoons. Robert got down on one knee and told her that he loved her more than anything in the world. Kaitlyn answered that statement with a resounding, "Yes!" After that, Robert presented the ring and finished asking Kaitlyn to marry him. It seems like they were on the same page already.