Jane and Jesse first met in the fall of 2022. Jane's cousin, Jessica, also a friend of Jesse's, invited the two to dinner unbeknownst to them. Jane was unsure about Jesse at this dinner, but the two engaged in conversation while Jessica and her fiancé Dakota were scheming. They hosted a cornhole tournament later that weekend and paired Jane and Jesse together on a team. They did not see each other or talk for a whole month after. Jane had a joint birthday party the following month, and Dakota and Jesse were there. Jesse would love to think that Jane couldn't stop thinking about him in the month between the meeting and the birthday party.

Unfortunately for him, that was not quite the case, but he knew he had an opportunity at the birthday party to win her over. Jesse loves to go two-stepping, and luckily for him, plenty of two-stepping would follow the party. He spun her around on the dance floor all night; the rest was history. Now Jane couldn't stop thinking about him and had to figure out how to see him again. Jesse was going to the fair the following week with a group of his friends, and Dakota invited Jane to join.

Jesse and Jane knew they had a spark during this fair outing, and Jesse knew he had to make a move before his time ran out. In this group, Jane said she listened to country music, and Jesse asked what type of country music. Jane, thinking on her feet, blurted out Taylor Swift. Jesse thought she was kidding but realized she was serious. Little did Jesse know he would be at a Taylor Swift concert eight months later.

Their time at the fair that evening was short, and Jesse knew this would be a great opportunity to tell Jane that there was so much more they had to see. The fair may not have been that important to either of them, but Jesse needed an in, and this was his chance. He asked Jane when leaving the fair if she would come back to see everything they had missed... but just the two of them. Jane seemed very excited and could not resist the opportunity to see even more of the ever-so-exciting Tulsa Fair, but really, she just wanted to be with Jesse. The two went back to the fair that weekend for their first date and talked for hours in the livestock arena where there wasn't even a show. That day was the beginning of a lifelong adventure, and the two quickly fell in love. Jesse attributes that first date in the livestock arena to slowly turning Jane into a real cowgirl, and Jane is so happy she found herself a truck-driving, blue-collar, God-fearing cowboy.