Charles and Hannah went to the same schools elementary through high school, but somehow they never had one class together! They ran in similar circles with Charles playing football and Hannah cheering, but it wasn't until many years later that they went on their first date.

Charles worked out with a mutual friend, PJ, who suggested he ask Hannah on a date. After that, they made plans to go out soon. The first plan was canceled when Hannah got sick, but Charles still showed his thoughtfulness by dropping off a care package at her door. The next date was decided on, but it happened to be on the day that Charles' family and friends were planning his surprise 30th birthday party. Thankfully, Charles' sister, Annamarie, reached out to Hannah to coordinate the date and surprise on the same day. Charles was totally surprised and their love started blooming that evening surrounded by his closest friends and family.

Hannah thought she was heading to a winery for a girls day with her roommates from college. She almost canceled due to an event at church, but her friend Amber said she was coming in town from Colorado, so Hannah couldn't miss it. The day ended up being rainy, but the girls found a spot outside at Kaya Vineyard & Winery listening to live music. Charles walked up with a rose and ring box and soon dropped to one knee. Right after Charles proposed, the sun came out, and it was a beautiful afternoon to celebrate. Both of their family and friends arrived shortly after to congratulate the couple and celebrate together.