Kevin and Aly started talking through an app and Kevin quickly asked Aly to go on a date saying "I make a better impression in person." The first date was at Bakersfield in Detroit for tacos and margaritas. Kevin invited Aly to go to another bar after, which she initially accepted, but then changed her mind as they started walking there and went home instead. However, she did have a good time and was impressed when Kevin proposed three great ideas for a second date. She chose the Moth at Marble Bar and they had such a fun night together talking and laughing. That date ended with their first kiss. For their third date, Kevin had been exposed to COVID and Aly had a trip coming up, so they decided to try a virtual date. Kevin suggested they both make cookies together since he knew that was something Aly loved. From that sweet gesture, Aly was smitten and knew that this guy was special.

Kevin and Aly decided together that they wanted to get married and how they wanted to celebrate their official engagement. Aly wanted a ring to mark the occasion and Kevin wanted a tattoo that represented how he felt loved and accepted for himself in this relationship. For the official proposal, they planned a trip to New York City, a place they both love and where they took their first trip together as a couple. They went to see a show and ate amazing food all weekend. Friday afternoon, Kevin brought Aly down to the Brooklyn Bridge where a photographer was waiting for them. Kevin got down on one knee in front of the New York Skyline and asked Aly to marry him. She said yes!