Myles began working with Lindsay at her school in 2021. Lindsay was the Assistant Principal and Myles was first a sub, then an employee. They got to know each other as friends, Myles bringing her Starbucks and McDonald's Diet Cokes and Lindsay becoming his confidant and trusted boss. As Myles tells it, he knew upon seeing Lindsay that she was going to be "something special" and "needed to be in his life forever." Lindsay was in the dark and completely unaware, she just thought he was a great employee and knew she needed caffeine! Weeks turned into months, months turned into years and along the way a solid friendship was built. Lindsay still thinking nothing of the friendship knew that Myles was struggling with his job and had talked him out of resigning multiple times. It was much different for Myles though, as he knew that he couldn't tell Lindsay his true feelings until he was no longer her employee. So he took matters into his own hands... He gave his resignation to the Principal (instead of Lindsay, knowing that she would talk him out of it). When Lindsay found out she was extremely hurt and upset that he hadn't come to her. However, as his 2 weeks notice neared the end, he gathered up his courage and on his last day at school he asked Lindsay out on a date and the rest is history.