Technically, Cheyenne and Michael first met in early childhood when Cheyenne's brother was in scouts with Michael and his brother. Their paths crossed multiple times over the years: Michael graduated in 2011, Cheyenne's brother in 2012, Cheyenne in 2015, and Michael's sister in 2018. Fast forward to May 2022, when the marching band at their shared alma mater, where Michael was working as the Percussion Tech, had an opening for a Color Guard Coach. Cheyenne’s former Coach, now the Twirling Coach, knew Cheyenne was still in the area and reached out to see if she’d be interested. Although it was never part of her plan, Cheyenne happily accepted the role. Cheyenne and Michael's official introduction happened at the following week’s band practice. Anyone who knows Michael understands that being quiet is his norm. So, when Michael began openly talking to Cheyenne, she felt a bit suspicious. Determined to win her over, Michael knew he needed the approval of Cheyenne's beloved four-legged friend, Athena. Since Cheyenne had a soft spot for sloths, Michael bought a stuffed sloth for Cheyenne to bring home to Athena. Although the sloth didn’t last long, Athena gave her first stamp of approval. Soon after, Michael and Cheyenne started talking regularly. To quote Michael's sister, "I knew it was serious when HE texted ME first." Michael eventually gathered enough courage to make things official halfway through band season, though he really only asked if he was supposed to take her on a date.

When Michael and Cheyenne first got together, they both agreed they would get married. However, Michael told Cheyenne she would have to wait at least a year before they got engaged. Cheyenne understood, but that didn’t stop her from looking at rings and sending them to Michael throughout their relationship. During their first band season, Cheyenne and Michael decided not to let the kids know about their relationship. By the second season, they were more relaxed—while they didn’t explicitly tell the kids, they were open to questions. As the end of the season approached and their anniversary drew near, some of Cheyenne’s students became suspicious. Cheyenne told Michael he’d better propose before the end of the season or the students would get even more impatient. Cheyenne was also growing increasingly impatient herself, knowing Michael had already asked for a list of all the rings she’d sent him, purchased a ring, and had something planned. Early on, Michael had said he’d ask Cheyenne’s local college friends to help pick out a ring, but Cheyenne warned him that coordinating with the two of them would be tricky without her knowing. Instead, he decided to keep them in the dark as much as he did Cheyenne and enlisted another college friend to help with the ring and to be prepared for when Cheyenne would call with the news. He also recruited a local friend to help with the plan. As October approached, Cheyenne knew they were nearing the one-year mark and asked the local friend to do her nails, just in case. When nothing happened by the time the first manicure wore off, they scheduled a second one. During that second manicure, they were invited on a double date with this friend and her fiancé, as well as another couple who were mutual friends. The day before the date, Cheyenne learned that the third couple couldn’t make it, but the second couple was still planning to attend, so Michael and Cheyenne decided to go as well. With the end of band season approaching and no proposal yet, Cheyenne had almost given up hope, especially as her friend who knew the details had convinced her it might not happen as soon as she hoped. On the night of the double date—which had always been planned as just that—Cheyenne texted the friend who had invited her, saying, “He definitely won’t, but wouldn’t it be wild if he asked tonight?” The friend, knowing exactly what was planned, managed to throw Cheyenne off completely. Cheyenne, hopeful yet suspicious, kept glancing at Michael’s pockets throughout the evening but noticed nothing unusual. Michael had always told Cheyenne he would only ask the question once, so she knew if he ever started to propose, she’d have to say yes. At one point during the date, Michael began to say the question, as he had been doing for weeks to keep her on her toes. Cheyenne responded as she always did: “Unless you’re about to get down on one knee and pull out a ring, you’d better stop that sentence right now.” Little did she know that, within an hour, Michael would do exactly that. As they were leaving the date and walking back to their cars, one of their friends told Cheyenne they had something for her. In true Cheyenne fashion, she made things difficult by moving around, causing Michael to keep adjusting his position. Eventually, he found the perfect spot and got down on one knee. Cheyenne couldn’t have said “yes” any quicker.