Kelsey's best friend Jori Blaiser played matchmaker. She showed Kelsey a picture of Jake and Kelsey instantly wanted to meet him. Jori showed Jake a picture of Kelsey to which he responded "Hello Kelsey!". The day after Kelsey moved back to Hudson from Houston, they decided to get dinner at Shanghai Bistro in Hudson.

Jake has always wanted to go to Maine. While their three boys went on a week long excursion with Jake's parents to South Dakota, Kelsey and Jake decided to set off on their own vacation. Their first morning in Maine, they had planned to go hiking and site-seeing around Bar Harbor. Jake was adamant about going to Somes Landing, a small beach area. When they arrived, there was a man taking pictures of the beach and the water, Kelsey thought nothing of it. They started talking about everything they had been through in the past 14 months, and how they can get through anything life throws at them from now on. Jake added "You know what else?" and got down on one knee. Afterward, Kelsey found out that the random man taking photos of the beach was actually set up by Jake as an engagement photoshoot!