Caitlin and Bobby's story began in August 2021 with a sweaty Justin Fields T-shirt. Caitlin had been helping with her aunt and uncle’s neighborhood garage sale all day. She was unprepared to go to the bar later that night, let alone meet the love of her life. Lucky for Caitlin, her brother gave her the shirt off his (sweaty) back so that she could attend. While Bobby wasn't unprepared, he was not expecting to meet the love of his life that night either. He was heading home from a friend's house when he had planned on stopping for a drink at the bar next door to where Caitlin was. After running into friends outside The Globe, he decided to go there instead. Caitlin and Bobby were placed exactly where they needed to be that night so that they finally found each other. After spending the evening at The Globe, Bobby and Caitlin couldn't get enough of each other. Coincidentally, they both had tickets to the Chicago Fire game the next day and decided to go together. They had their first official date later that week at Rocks in Lakeview. Caitlin and Bobby quickly fell in love and knew they were meant to be together. Later that fall, Bobby and Caitlin attended Riot Fest together. They were headed home when a man told them "she had love in her eyes." This exact moment is when Caitlin knew she was in love. Just a few weeks later, Bobby shared that he felt the same way. For their third dating anniversary, Bobby planned a little getaway to a bed and breakfast in Wisconsin. Caitlin had no idea that he was going to propose. Apparently, Bobby forgot too since he left the ring in Chicago, but he was able to have Caitlin's sister overnight the ring. The proposal was perfect. To this day, Caitlin and Bobby are still as in love as they were that night home from Riot Fest.