Myles and Jenna "met" on a dating app called Tinder, and casually talked for a few months before spontaneously deciding to meet in person. She was in downtown Rapid City at a wine festival with some friends and he was at his favorite bar, Paddy O'Neill's, where he had rode his motorcycle down for a Guinness. Once they found out they were near each other, they decided to meet for a drink in person. They only had an hour before Myles had to be to the airport and off to Seattle, but that was enough time to know how they felt. The connection was pretty instant and within less than a month, Myles had already met Jenna's family and the two had become "official".

Jenna and Myles had planned a trip back to Rapid City around the 4th of July. Jenna was in a good friends wedding that following weekend, so they decided they would make a vacation of it and enjoy some time back in Rapid City. The couple went down to Jenna's family lake house to spend some time on the water with family and friends. After getting off the water on the 4th of July, everyone got ready to grill out for dinner and hang out by the fire (like they always do). Myles asked Jenna if she would take a picture with the sunset in the background, and she of course said yes. This wasn't an abnormal question to Jenna, because the previous summer they had taken a picture there as well. When the two posed for the picture, Myles turned and asked Jenna to marry him. And of course she said yes! The best part about the proposal was that Jenna had NO IDEA it was going to happen (she's hard to surprise), and also that some of their closest family and friends were there to share the joy together! Myles and Jenna are very excited to spend the rest of their lives together.