They met after Caitlin's coworker and Andrew's best friend's mom, Carrie, set them up on a blind date. In the fall of 2024, they went apple picking at Kercher's Apple Orchard. The date continued as they made apple crisp at Caitlin's house and sat on her patio talking late into the evening. Their second date quickly followed the next day at Goshen Brewing Company where Andrew suggested a date for a third day in a row, but Caitlin said, "that's too much too fast." Three weeks later, Caitlin called her mom and told her she was going to marry this man.

Caitlin introduced Andrew to her parents just a few weeks after they met over dinner at their house and Andrew introduced Caitlin to his parents at Thanksgiving a few weeks later. She fit in with his family and he with hers, confirming what they thought they knew - that they were each others' person. Caitlin introduced Andrew to the rest of her family at Christmas, and Caitlin's brother Andrew Hooley liked Andrew Weddle immediately, but spent Christmas calling him Andrew #2. Andrew came along to the Hooleys' house in Florida in January, their first family vacation together. They love spending time at wineries (Andrew asked Caitlin to be his girlfriend at Tabor Hill Winery the day after Valentine's Day) and they impress each other often with their chef skills as they love to cook for each other.

Caitlin's parents planned a surprise 30th birthday party for her brother, Steven, inviting family and friends to their house in July. They planned to take quick family photos so, according to Caitlin's mom, "she wouldn't show up in jean shorts and a t-shirt." Caitlin dressed up for what turned out to be a big night! Andrew pulled her and their parents aside after the family cut Steven's birthday cake and dropped down on one knee to ask her to marry him. Enthusiastic cheers rang out from all the family and friends watching from the patio and everyone joined in a Champagne toast!