Jessi and Keegan met on a dating app in Fall 2014. It was Jessi's last Tinder date and Keegan's first. They met IRL in Decatur at the Square. Although Keegan didn't know how well he was doing, after making her laugh and letting loose his long red hair (Fabio style), Jessi was smitten. They continued dating over the holidays and by spring, both knew there was something special happening. A couple of months later, on a date to the Atlanta Botanical Gardens, the couple were exploring a small corner of a greenhouse when Keegan turned on some music. They slow danced beside a water fountain to 'I Don't Want to Set the World on Fire' by The Ink Spots. Keegan said, "I think I love you." And Jessi replied, "I know that I love you."

In November 2018, months after secretly picking out an engagement ring, Keegan suggested a date night at the Botanical Gardens to see a special exhibit. It had been a hot minute since the couple had been, plus, he had a Groupon (Spoiler Alert: there was no Groupon). Keegan led Jessi through the gardens to the greenhouse. As they explored, Jessi began to hear music and recognized the song. They found their little corner and began to slow dance. Keegan got down on his knee. He asked, "Will you marry me?" She replied, "Yes!" They were then met with the flash of a camera, paparazzi style. Keegan had asked Jessi's photographer friend to help him capture the moment. After an impromptu engagement photo session, the couple went to Jessi's favorite restaurant to meet with their family and friends to celebrate.