In May of 2020, Jesse was brought to Corpus Christi to train at NASCC to fly multi-engine aircraft. Cassidy had been living in CC working at the Omni Hotel as the Pastry Chef, however, at the time she was furloughed due to COVID-19 leaving her with a lot of extra time on her hands. Jesse was scheduled to only be in Corpus for roughly 6 months and was not planning on anything permanent but God had other plans. Introductions began with Hinge and ultimately led to Jesse asking Cassidy to go to the beach for a doggie playdate with their aussies, Koba and Tex. God definitely has a sense of humor with how this date went. The two pups got into a barking match and a quick tussle before even getting to the sand. Cassidy was ready to pack it up, but Jesse was determined to enjoy those mimosas on the beach, pups happy or not. The next few dates involved walks with the dogs to force them to become friends and slowly but surely that they did making Cassidy and Jesse's time together easier and easier. And as they say the rest is history.

One quality of the proposal that Jesse was adamant about was catching Cassidy off guard and surprising her. After secretly asking her father for her hand and her mother for her permission he was given the green light to propose. Jesse reached out to Cassidy's childhood friend, Maddy, to enlist her help with the proposal. The Christmas tree in downtown Corpus Christi was chosen as the location and a plan to get Cassidy to the tree unsuspecting and dressed cute was created. Jesse and Cassidy had previously taken pictures at the tree a couple of weeks prior so Jesse asking for a second round of pictures would've been suspicious. In comes Maddy with an invite to Cassidy for couples pictures the following day, Dec. 23rd, with Maddy and her fiancé, RJ. The plan was off to the races. Cassidy asked Jesse if he wanted to go with Maddy and RJ to which he of course said yes. Jesse secretly was chuckling as little did Cassidy know she had just invited him to her own proposal. The day of the planned proposal arrives and Cassidy was not feeling well. As much as Jesse tried to nurse her back to health she cancelled her plans with Maddy and spent the day in bed. Jesse was sent scrambling to come up with plan B. Christmas Day arrives and after spending the morning with Cassidy's family Jesse reached out to Maddy again. Maddy said that RJ had to leave Corpus for work and was no longer able to come so Jesse had to think of a way to get Cassidy downtown without tipping her off. After some thought Jesse recruited Cassidy's brother, Kennon, and sister-in-law, Josephine, for their help in getting her downtown. Over dinner the two casually dropped the idea of taking Christmas pictures at the tree but needed a photographer to which Cassidy volunteered to do. After dinner was over the four went downtown to the tree and began taking pictures. Jesse and Cassidy were up and Maddy arrived to witness Jesse get down on one knee and ask Cassidy to spend the rest of her life with him.