Colby and Kayla matched on a dating site. After talking for several weeks they decided to go on a date together. The date was supposed to start at Texas Roadhouse and go from there, but their wait time was over an hour. Together they decided to go to Hickory House BBQ instead. Rather than driving both cars, they took Colby's truck. Though Colby won't ever admit it, he fell in love with Kayla as soon as he heard her loudly cuss out a Texas driver who had cut them off on their way to the new restaurant. After eating a delicious dinner, they weren't ready for the night to end. They decided to go see the new Wonder Woman movie together. However, the start time for the movie wasn't for another hour. With time to spare, they went to Second & Charles, Kayla's favorite store, and browsed all the movies, books and nerdy odds and ends. After the movie, they stayed in the car and talked for hours. It was that night they decided to put a label on it and start a relationship.

Colby carefully planned and kept secret the entire proposal plan. After asking Kayla's father for his blessing, he got both his family and hers to agree to Thanksgiving together. A week prior, Kayla had been looking at the ring she and Colby had picked out, only to find that it had been marked as clearance and was then sold out. Colby feigned total incompetence, but promised he would figure it out. On Thanksgiving all of the families gather together, ate and partied until it was time for the family photo. After Kayla was directed to stand in the middle of the family, Colby was assigned to take the picture. After taking the photo, he approached Kayla, "In the spirit of Thanksgiving, I want to thank you for teaching me what love is, and for being patient with me, will you Marry Me?". Of course, Kayla said YES! (Or you wouldn't be here). After opening the ring box, it was revealed to be a Ring Pop that held the ring Kayla had been freaking out about losing. Kayla then promptly called Colby a Liar, and told him to put the ring on her. The second best part was everyone else in the room having known what was going on the whole day, and no one uttered a single word!