Kayla and Dylan met at Monroe High School in Wisconsin and became close friends. Dylan was excited that Kayla was interested in more than a friendship, and he knew he had to lock that down immediately. Things became more serious as Kayla planned for her future, sending her off to Iowa State University. Two years later, Dylan began college at Marquette University. Being away from each other and family was difficult, but it only brought them closer together. Their relationship was truly tested when Kayla studied abroad in Rome, Italy for a semester. But through the tough times, their bond grew even stronger. They were finally able to move in together and enjoyed fun times in Milwaukee and Boston. Where will the adventure take them next?

Kayla scored Luke Bryan tickets at Summerfest for both the Starck and Streff families. Dylan was able to sneak away with Steve and have an important conversation. Steve gave Dylan his blessing to ask for his daughter's hand in marriage. Emotions were running high that night, and the news spread quickly. However, the surprise was not ruined for Kayla. Kayla had just completed a grueling two weeks of work at the musical festival. Dylan treated her to a couples massage that following weekend. Then they packed their bags to go home to Monroe. But first, Dylan had another surprise. He took her to the lakefront for a romantic picnic, which included all of her favorite foods. He was anxiously waiting to propose, but Kayla was only interested in eating her food. Dylan began telling Kayla about the night of the Luke Bryan concert, when he reached into his pocket and presented the engagement ring. Kayla instantly began to cry and said yes! Dylan's sister, Dana, was waiting close by and took photos of the newly engaged couple. The celebration continued as they met their families at their favorite restaurant. It was a perfect way to finish the best day of their lives so far.

Dylan and Kayla decided to take a spontaneous trip to Martha's Vineyard. They enjoyed the ferry ride to Oak Bluffs, where they began their journey on the island. They rented bicycles and rode from town to town. They absolutely fell in love with Edgartown, where the views are spectacular and the food is just as amazing. They both knew this was the perfect place for their intimate wedding.