Tyler and Jenny met in 2015 when their friends, Heather and Jon, were planning their 2016 wedding. Jenny was the Maid of Honor and Tyler was one of the Best Men. Jenny visited Heather to try on bridesmaid dresses one weekend, and the girls, along with Jon and Tyler, met for drinks. At that time, Jenny was in a relationship. Tyler reached out to Jenny via Facebook on Valentine's Day in 2016 to ask if she was ready for the upcoming wedding (by this time she was single). They chatted (a lot) over the next few months and officially started dating on April 1, 2016. They dated long distance for one year before Jenny moved to Rochester, MN, to be closer to Tyler. In 2021, they moved to Tyler's grandma's farmhouse near Byron, MN. Tyler proposed on December 15, 2023, by writing "Marry Me?" on a cow ear tag and hanging it on their Christmas tree for Jenny to find.