Both fed up with dating, Aaron and Kelsey ended up being each other's last date from OKCupid. The first date was a success as they spent four hours talking over dinner at a local restaurant. The following dates would continue the trend of increased interested from both parties and on Aaron's birthday, he asked Kelsey to be his girlfriend.

After dating for just over a year, Aaron proposed to Kelsey at one of her favorite parks in Denver, City Park. A month prior, they found themselves ready to make the next big step in their relationship. A trip to Shane Co. would lead to them picking out a ring together. Aaron kept Kelsey on her toes by building the anticipation of when he would pop the big question. Would it be on his annual work conference trip in Montana? Would it be on their one year anniversary? Or would it be while Kelsey was playing a show? None of these situations would lead to a proposal. A perfect early morning picnic on the first day of fall would be the moment where Aaron would express his everlasting love for Kelsey by asking her to marry him.