They meet through Bumble - Jennie will always say she swiped right by mistake after a few too many glasses of wine. Despite this, they ended up sharing some small talk on their hobbies/interests. Andy worked up the courage to ask Jennie out on date, however, Jennie said she couldn't make it. Andy decided to drink away his sorrows and go out with his friends. They went to watch an Iowa State game at a pub, but he left the invite open. Later that night, Jennie came out to join Andy and his friends. They had a great time getting to know each other while bar hopping, and continued to chat even after all of Andy's friends went home. The rest is history.

Andy and Jennie had gone shopping to look at engagement rings a week prior. Little did Jennie know that Andy purchased the ring that she loved just a couple days later. Andy was planning to propose on the weekend, however he knew Jennie would expect it if they went on a fancy date. Andy got together with his future sister and brother-in-law to come up with a plan. That Thursday on August 5th was the perfect evening, as Jennie just finished a long shift at work, and she was exhausted and tired. She was not looking to cook or get made up to go out. Andy suggested that since she had had such a hard day, that they should go somewhere new to get her favorite dish - Salmon. They found a great place called Skip's that served the dish. With a little bit of effort (OK maybe a lot of effort), Andy convinced Jennie that a relaxing evening would be worth the little effort to get dressed up. They shared a lovely meal and split a bottle of wine. Meanwhile, Jennie's sister and brother-in-law were at Gray's Lake with their nephews, waiting to set up the perfect surprise. As their meal came to an end, Jackie called Jennie to stop by and go on a walk with the family. As the moment drew nearer, Andy became nervous because the box that the ring came in was pretty big and he had nowhere to hide it. Luckily, he was able to get in her purse by incessantly asking for a tissue and demanding to search her purse himself for one. Jennie, choosing to ignore how weird Andy was acting, took his hand as they began walking up to the bridge. The scenery was beautiful with Gray's Lake and downtown Des Moines in the distance. Jennie's brother-in-law suggested Andy and Jennie take a picture together, since they were dressed up so nicely. Standing behind them was Jennie's nephew with a sign - "Will you Marry Me?". (Brooks also had a sign that said "Will you be my Uncle Andy?") As she turned around, Andy got down on one knee. Jennie was speechless for a moment, but then she (and Andy) finally said YES!