While living in College Station and attending college, Jacob worked at Wolf Creek Lube, an oil change shop. Jessica was using her dad's old Chevy as her daily driver and needed someone to take a look at it, as it was starting to act up, as old trucks do. She asked a friend for a recommendation on who she should take the truck to, and they said they knew a guy named Kessler who worked at Wolf Creek Lube. So a few days later, Jessica pulled up to the shop and was greeted by "Kessler", who took one look at the truck and said "let me go get the other manager, he'll take a look at this for you." It turns out Jacob was in the middle of repairs on his own vehicle when Jessica showed up, so he didn't want to bother wasting time on her and her truck when he could be finishing the work on his own vehicle. A few days later, Jacob ran into Jessica at Hurricane Harry's. He instantly regretted not sticking around to help Jessica with her truck problems and decided it was a good idea to use some of his terrible pick-up lines and dad jokes on her to make up for ditching her at Wolf Creek. Jessica did not approve of this and pretty much ignored every line and joke Jacob tried to use. A few weeks later, Jacob ran into Jessica at Harry's again. He tried more terrible pick-up lines and dad jokes, but again, Jessica was not having it. He ended up leaving early that night and noticed Jessica's truck parked next to his car. He stuck one of his prestige business cards into her door handle, hoping she would see it when she left. Jessica found the business card later that night and scoffed at Jacob's persistence. But the move worked. The next time Jacob and Jessica bumped into each other, Jacob joked about how offended he was that Jessica hadn't reached out to him, claiming she hated his guts. Jessica felt bad and shot him a text the next day, saying, "It's Jess. And by the way, I don't hate you." Now that Jacob had Jessica's phone number, he made his next move. He decided to strike up a conversation with Jessica's best friend at the time and quickly got on her good side. He thought this would help Jessica soften up toward him, but that did not happen. Jessica's attitude toward him hadn't wavered much and he was starting to give up on asking her out. Jacob's friend, Rob, happened to have tickets to a Tracy Byrd concert in town and offered Jacob two free tickets. Jacob almost turned down the tickets, but decided to make a last ditch effort and ask Jessica out one last time instead. He messaged her, asking if she would go with him as his date. Little did Jacob know, Jessica was with the friend he had struck up conversation with. She convinced Jessica to give him a chance. So, Jessica responded to Jacob's message with "Sure! But only if it's a friend date :)". Jacob saw that as a win and ran with it. He decided he was going to take full advantage of the opportunity and pull out all of his best tricks. The morning of the concert, Jessica met Jacob at Mi Familia, a Mexican restaurant with a breakfast taco buffet. She decided he wasn't half bad and agreed to let him drive her to their next stop of the day - a flea market. After walking around for a good hour or so, Jacob bought Jessica an aloe vera plant and told her "This plant is a symbol of our love. If it dies, you're dead to me." Jessica laughed at his overbearing confidence and accepted the plant. After breakfast tacos and a trip to the flea market, the two proceeded to the concert and had a blast. Afterwards, they went to Whataburger for dinner, where they sat and talked for hours before finally calling it a night. By the time Jacob dropped Jessica back off that night, Jessica had realized he wasn't half bad and that she enjoyed the time spent with him. Two weeks later, they went on their first official date. Now, three years later, the two have a thriving aloe vera plant and still argue over whether the Tracy Byrd concert was really their first date.