Ryan began his freshman year at Woodgrove High School in 2011, while Rachel was entering her sophomore year. Ryan was involved in football and basketball, and Rachel was on the varsity softball team. Throughout high school, Ryan became friends with Rachel's younger sister, Lindsay, and eventually he became friends with Rachel too. Rachel graduated in 2014 and went on to Virginia Tech. A year later, Ryan ended up at Virginia Tech as well. Rachel and Ryan blended their college friend groups and hung out often. After graduating from college in 2018, Rachel moved back home, then eventually moved to Arlington with her friend, Eliese. After Ryan graduated in 2019, he moved back home as well. A few months later, Ryan was at Rachel's house in Arlington for a Halloween party. He was dressed as the Green Bastard, and Rachel was dressed as an old lady. Ryan had the courage to ask Rachel out one more time (after being rejected a few times in college). This time she said yes, and the two have been inseparable ever since.

On this beautiful, sunny Saturday, Ryan and Rachel had planned to meet up with their friends, Eliese and Chad, at a local winery. Ryan had stated that he needed to stop to at Rachel's aunt and uncle's house to help her cousin, Corey, with something before they went to the winery. Ryan "took the wrong turn" to go to Corey's house, and said that they would just go the long way instead. This longer way, would take the two of them right past the house that Rachel grew up in. Right next door was the house that her grandparents had lived in, and where many childhood memories still live. As Ryan drove past this house, he slowed, and eventually pulled into the driveway. On the tree next to the driveway was a banner that said, "Will You Marry Me?" Ryan and Rachel got out of the car, and walked hand in hand over to the tree. Ryan got on one knee, and asked Rachel to marry him. What makes this moment even more special is the fact that Rachel, her father, and both of her sisters have a tattoo of this exact tree. Ryan knew how much this place meant to Rachel, and asked the current owners if he could use it for their special moment. When they said yes, Ryan started planning.