Andrew and Destinee have been told that they knew each other as kids, however neither of them remember this. They met again as adults at a mutual friend's Celebration of Life in August 2021. Andrew asked his cousin, and Destinee's friend, Natalie, if Destinee was single. However, at the time she was not, by October 2021 Destinee was single, and the couple were reconnected through Natalie.

Andrew and Destinee had their first hangout online with Natalie and her brother, where they played some video games. According to Andrew, Destinee healed his character in a way that was not deemed necessary and he found this an attractive quality. The very next day Andrew started messaging Destinee. A few days later, on October 17, they had their first date.

In November, Andrew asked Destinee to attend his friend's wedding in Barrie. He claims that it was at this wedding that he fell in love with Destinee (probably when she ate a burger when they got back to the hotel before changing out of her wedding clothes). It took Destinee a little longer and she told Andrew that she loved him while playing a video game (Animal Crossing) in January 2022.

On October 21, 2022, Andrew and Destinee were celebrating their one year anniversary , which was on 17 October. Andrew took Destinee to a trail in Dundas, overlooking the Hamilton escarpment and proposed. When he got down on one knee and asked Destinee to marry him, her response was "obviously!"