Kimberly wasn't always interested in Ryan, but during a shopping trip with mutual friends in 2019, she realized that Ryan wasn't so bad after all. In the week leading up to their first date, Ryan tried so hard to convince Kimberly to come over to his apartment for dinner, but she kept telling him, "No we will just wait till this weekend".

The weekend of their first date arrived.

Kimberly and Ryan's first date was on a fall evening at Vesperman Farms in Lancaster, WI. During their first date, Ryan found out how much Kimberly was bad at knowing which direction to go in the corn maze. Although, after making multiple wrong turns, they both came out of the corn maze with success, as doing a corn maze would be checked off Kimberly's bucket list.

After Vesperman Farms, Kimberly and Ryan had pizza for dinner and watched movies the rest of the date.

April 3, 2021 started out with Ryan and Kimberly going to the shooting range in Wausau, WI, where Ryan and Kimberly had their first date in Wausau. Before meeting Ryan, Kimberly had never shot a gun before so guns were a new experience to her. Ryan always explained gun safety to Kimberly and the importance to never point a gun at a person, unless their was an intent to shoot someone.

After the shooting range, Ryan and Kimberly met up with Logan and Danica; where they went to the top of Granite Peak. Ryan was waiting patiently for it to get closer to sunset; as Kimberly thought they were just going for a walk and wasting some time before going to get Dinner.

During their walk, Ryan told Kimberly to sit on a rock and look out to the view of Wausau. While Kimberly was looking into Wausau's horizon, Danica was trying to distract her from not turning around, because Ryan was taking a picture of the engagement ring with Kimberly's back to him.

Ryan decided that they should walk to the observatory tower and walk to the top to take a view at Wausau before the sun officially sets. While at the top, Danica and Logan took pictures with Ryan and Kimberly and took pictures of Ryan and Kimberly. After one picture, Ryan got down on one knee and asked Kimberly to marry him. Of course Kimberly said "Yes!"