Both Nick and Jackie were coaching sports at the same middle school in the fall of 2019. Nick coached football and Jackie coached cross country. After recently being promoted to the head coaching position, Jackie had many questions about the responsibilities she'd be taking on. One day, while meeting with the Athletic Director (who was also the AD when Jackie was a student there), Nick was called in to assist with answering questions. Sparks flew between the two instantly! Nick remained patient with Jackie and all of her questions as the season began, and he started pursuing her through casual conversation before practices. A friendship had blossomed and continued to grow throughout the season until the last day of practice when Nick FINALLY asked Jackie out.