On August 17, 2017, Ashlyn followed her GPS and parked on the wrong side of a large street outside of Caleb's house. As Caleb crossed the street to meet her, his roommates watched out the window as they hugged hello for the first time on a road median. Their first date consisted of dinner and an outdoor concert in the park (an Eagles tribute band). Caleb thoughtfully brought two sweatshirts just in case Ash got cold, which she did. Little did she know, the sweatshirt she wore that night would stay with her in the years to come when she was apart from Caleb during his deployments.

The two saw each other often over the next few weeks. At the time Caleb was at Port Hueneme, California for Civil Engineering Officer training school and Ash was home for the Summer. At the end of September, Ashlyn had to move away to finish her last year at UC Irvine but didn't want their relationship to end. She drove back the very next weekend to see Caleb. After that, one of them would make the two-hour drive up or down so they could see each other regularly.

In July of 2020, Caleb started looking at rings. He finally bought one in December 2021. When Angela, Ashlyn's mom, visited for Christmas, he showed her the ring with a band he had custom-made for her daughter and asked for her blessing. To capture the moment, he found a photographer well versed in engagement photography. He wanted to choose a location that would reflect his home state of Oregon with greenery, Ash's home state of California with ocean views, as well as the state they were in with Hawai'i's beautiful volcanic rock. He found Makapu'u Beach just before sunset to be the perfect place. By February 2022 he had the ring, place, and the plan. Finally, he called Ashlyn's father figure, Joe to inform him of his intentions and ask for one last blessing.

On February 20, 2022, Caleb took Ash to a couple's photoshoot to get some "nice professional pictures of the two of us." After the photographer gave him the que, he hugged her close, kissed her, and got down on one knee. As the ocean splashed salt water into both of their tear ducts, she said, "YES!"

On October 8, 2022, Caleb and Ashlyn will get married in a small ceremony in Honolulu, HI. Although they wish everyone they've known and loved could join them in person on this day, due to ever-changing travel restrictions, they've made the choice to gather their parents and siblings together for this day and look forward to celebrating with others in the future.