Dylan and Darrah met in November 2013 during set construction for the play "Silent Laughter." Darrah was painting details on the house while Dylan was constructing a bed to collapse. The stage manager - a mutual friend - called Darrah over to see the bed. It was then Dylan and Darrah were first introduced.

September 6, 2014: Dylan took Darrah to the Dahl Arts Museum and the Journey Museum in Rapid City, SD. They then went on a hike outside of Rapid City and "geologized."

September 5th, 2015: Dylan took Darrah on a date to celebrate their first anniversary and kept it a secret until the day of. He took her to The Mammoth Site in Hot Springs, on a tour of Wind Cave, and finally a picnic on the trail they hiked on their first date which ended with a proposal and a ring.