After matching on Hinge, Tyler quickly asked Courtney out on a date. They met on October 8th, 2023, for lunch on a Sunday afternoon at Farm & Craft in Old Town Scottsdale. The conversation flowed and lunch quickly turned into getting ice cream, as well. After, Tyler walked Courtney back to her car to say goodbye and said, "I like you! We should do this again." Surprised, but loving of his forwardness, she agreed! Their second date was spent at Tempe's Oktoberfest celebration where the two ended up dancing to a live band for what seemed like all night, and it felt like a perfect date. The next day, Tyler took Courtney on a picnic in Fountain Hills where he brought a fully packed picnic including snacks, homemade salads, and desserts. After that, they were hooked on one another from there on out.

After dating for almost two years, Tyler decided to pop the question! The two had just started their first European getaway together traveling to Switzerland and Germany. On their third morning of the trip, in Zermatt, they took a cogwheel train ride up into the Alps for stunning views of the Matterhorn. The cogwheel ride has one too many "technical difficulties", including sliding backwards on the mountain and the emergency brakes having to be thrown on (twice!). Tyler decided it was a day they'd never forget, and the perfect day to ask the big question. Just as they started their hike down the mountain he suggested taking a photo and set up his camera with self-timer. Surrounded by nothing but stunning views, Tyler asked Courtney to marry him. The easiest "yes" of her life! After hiking down part way, the two celebrated with Swiss shandies at one of the mountain rest stops. They enjoyed the rest of their trip on their engagement-high.