Caitlin and James' story began on a lively evening at a local Chili’s where Caitlin worked as a bartender. On this particular night, Caitlin was handling an unruly bar guest named Phillip. Amidst the chaos, James walked in with his best friend Kevin. James immediately noticed Caitlin. James and Kevin became regulars at the bar, and James made a point to tip Caitlin generously, leaving more than the usual amount for a simple $3 beer. His kindness and consistent gestures stood out, and it wasn’t long before he asked Caitlin out to a Sharks vs. Kings hockey game, marking the beginning of many games they would attend together. Their connection deepened further when Caitlin went to Europe for a month. During her travels, she stayed in close touch with James, FaceTiming him more often than she did with her own family, showing just how important he had become to her. When Caitlin returned, James wanted to make their relationship official in a memorable way. He asked her to be his girlfriend with a bouquet of flowers and her favorite perfume.