Despite going to the same school for a year, Austin and Jenna had not yet met each other. Austin's 8th grade English teacher advised Austin to take Honors English his freshman year of High School. This made Austin nervous to be in a "smart kid" class. Some of the semester went by, but Jenna and Austin never really spoke to one another. It wasn't until Ms. Macias put them in a new seating arrangement that Austin started to talk to Jenna and noticed how beautiful she was. Jenna couldn't help but laugh at Austin's jokes. He was goofy yet still charming. One day, the class was to watch a movie about Greek gods, but Austin and Jenna exchanged phone numbers instead. Austin made it a priority to walk Jenna to lunch. After the first semester, the two were no longer in the same class, so Austin found a new way to talk to Jenna during class. He would leave page-long notes in her class textbook, and she would write him a reply for the next day. Pretty soon Austin was asking Jenna to come over to his house. With his parents permission their first date was set. His sisters helped him pick out an outfit and Jenna's oldest sister, Nichole, dropped Jenna off. The two watched movies downstairs and Austin taught Jenna to hacky sack. Austin knew that homecoming was coming up, so he asked Jenna to the dance. However, Austin did not want to go as "just friends". He wanted them to be so much more than that. With the night nearing it's end, Austin needed to do something fast. Nervous and not knowing what to say he ran upstairs and grabbed a marker. Returning to Jenna he awkwardly held out his hand with the words, "Will you be my girlfriend?" on it. Jenna accepted wholeheartedly. Even though the two of them were only freshman, they both knew someone very special had entered their lives.

Sunday December 22nd, 2019 Austin took Jenna on "date night" for dinner and to see Star Wars: Rise of Skywalker. Austin had put together a detailed plan with Brier for after the movie. Brier recruited his friend, Larry, and they set up a caricature stand in front of the Christmas tree at Old Towne while the movie finished. Austin walked Jenna out of the theater and casually mentioned to go check out the tree. Jenna excitedly noticed Larry's stand! Austin had never done a caricature with her before, so Jenna was excited and was wanting to sit for one! Austin gave in to her wishes... ;) Larry faked a story about how he was an art student trying to gain experience. He pretended to sketch an elaborate caricature for 10 minutes, finally to reveal his work. The picture Larry presented was actually a caricature Austin had a real artist sketch a week prior that read, "Will you marry me?" The caricature showed Austin kneeling, Jenna gasping, and an added touch of Wally! As Jenna read the caricature, Austin was heading down on one knee. As Austin finished asking, Brier came out filming from behind the Christmas tree to finish off the surprise. It took Jenna a second to even realize Larry was a fake! Larry had been pretending to sketch the caricature, but for believability, he was sketching his own. His drawing added in some extra laughs and helped top the evening off as one truly unforgettable night!