Kyle and Hailey met at Cooke Canyon Hunt Club, where they worked as Bird Handlers in Ellensburg. While both were attending Central Washington University. On Kyle's first day of work, he was introduced to Hailey while she was cleaning dog kennels. Hailey could not hear Kyle and their coworker calling out to her since she was wearing headphones, so Kyle threw pebbles in her direction, which then caught her attention. From then on out, they would spend mornings catching birds and talking out in the fields while they waited for hunters to arrive. It truly felt like they had known each other their whole lives. The first time Kyle and Hailey spent time outside of work together was when he invited her to his apartment to meet his family dog, Remi. Here, he would cook Hailey dinner while she worked on her homework and they binged watch their very first show, "Invincible" Their first official date was for Hailey's 21st birthday in November, where Kyle took her to The Pearl and to her first college bar (The Frontier and Club 301) later that night. Kyle and Hailey spent their first Thanksgiving together that same month, where he finally asked her to be his girlfriend on November 26th, 2021.

Kyle proposed to Hailey on a camping trip at the Tucannon Campground. He chose this location because of its significance to Hailey. She grew up camping and fishing here with her family. Kyle and Hailey spent the morning fishing at one of the Tucannon ponds. He got on one knee while she was reeling in her lure. He presented her with a beautiful moss agate ring, and she said yes!! They spent the rest of the afternoon soaking in a creek with their dog Teddy.

Kyle and Hailey welcomed their firstborn son on September 14th, 2025. Rowan Stuart Simmons was born at 3:08 in the afternoon at 8 pounds 14 ounces and 21.5 inches long.