Connor and Claire first met in summer 2017 while working as interns for the Kane County Cougars. At the time, they were just friends, but Connor secretly had a crush on Claire. They both returned to college and kept in touch occasionally. Fast forward to summer 2018, Claire had graduated college and needed a job. Meanwhile, Connor had been promoted at the Cougars. Their paths crossed when Claire went to a game with her dad and spotted Connor running around the stadium. They didn’t connect that night, but Connor later called Claire to say the Cougars had an intern spot open and suggested she come back to work for the team! A few weeks later, Claire was back at the ballpark. On her first day, Connor greeted her with a hug, and this time, something felt different for both of them. They kept things professional at work, but as the season was winding down, Connor finally asked Claire out. Their first date was a Chris Young concert, and two months later they became official!