In June of 2014, Annie went to a wedding with her best friend from college, Amy, in Northern Ohio. Amy's cousin Rachel was marrying John's brother Ryan, and John was the best man. After the reception, with some encouragement from Rachel's sisters, Annie walked up to John to introduce herself and John promptly walked away, preoccupied with taking care of his cousin. Thankfully, Rachel's sisters swooped in to save the day and allowed John and Annie to properly meet. Five days later they went on their first date and have been together ever since.

Every summer John and Annie visit the Sweeney Family's house on Lake Mecosta in Michigan for the Fourth of July. It became their tradition to stay a day or two after the rest of the family left and they would always kayak out to "the island." They took their usual kayak trip to the island and wandered around in the shallow water. John secretly set up his camera to record, and in true Annie-fashion, John could not get her to stand still long enough to start proposing, so he had to start while her back was turned. The proposal was intimate and perfect and John proposed with a ring he had secretly purchased the year prior because Annie had fallen in love it when she first saw it. :)