In March of 2022, Madi was invited to a party at Kolby’s Santa Monica apartment by their mutual friend, Izzy. Before the party, both Madi and Kolby had secretly been shown photos of each other on Instagram. When Madi arrived, Kolby immediately turned on the charm and walked right up to her. She was wearing a grey plaid blazer, and—by coincidence—Kolby had the exact same patterned coat in his closet. He insisted they take a picture in their matching jackets. Later that night, Madi and Kolby ended up at the Doheny Room in West Hollywood, where they connected over Jägerbombs, stomach sensitivities, and KU basketball. The conversation inspired Kolby to put Kansas winning all four of his March Madness brackets (which ended up happening). Before the night was over, Kolby convinced Madi to go on a casual, hungover date at Tatsu in Sawtelle the next day, where he watched her eat ramen for the first time. About a month later, Kolby planned a full date day: Café Gratitude, paddle boats in Echo Park, the Griffith Observatory, and finally the beach in Malibu, where he had a picnic and sunflowers—Madi’s favorite—waiting. There, he asked Madi to be his girlfriend. Over the next three years, Madi and Kolby grew together. Madi taught Kolby how to make tasty soups, showed him her life in Kansas, helped him become more thoughtful (it was for the best), and watched him become a father to Marigold. Kolby showed Madi his favorite West Coast spots—including Big Sur, Mexican wine country, Zion National Park, and Mammoth Mountain—and pushed her out of her comfort zone with new activities like camping, skiing in a blizzard, and distance running. In September of 2025, Madi flew to New York to “spend time with Kolby’s sister Kylie and her family.” A week beforehand, Kolby had told her that he and Kylie spontaneously decided to book rooms at a resort in Montauk for a small getaway. Madi had no idea he had actually been planning the trip all summer, and that Kylie and her family wouldn’t be joining. On the evening of September 19, 2025, Kolby took Madi to Shadmoor State Park, to the cliffs at the end of Montauk, where a photographer and engagement setup were waiting. When Madi saw it from afar, she assumed someone else was getting engaged—until she noticed a photo of herself. She said yes, and it instantly became the best day of their lives (so far). The following week, they moved to Austin, Texas, as an engaged couple, ready to build their new life together.