Cailin + Drew have known each other since high school. A few years after graduating they were both single and their best friends were dating. Their friends convinced them they’d be perfect together…..and here we are nine years later! Cailin’s favorite part of their first date was when Drew said “I really like you” As for the proposal, it was the night before leaving for Aruba, so they were running around getting ready. Cailin had just gotten home from getting her nails done. Drew was acting funny playing with their cat Kitcat. When Kitcat came over to greet Cailin she had a box in a bag tied to a bowtie on her neck. Cailin was trying to get it off of her when Drew knelt down next to her and proposed!