Kaitlin and Stephen met in 2018 via Kaitlin's twin sister, Sarah (center). Stephen met Sarah where he volunteered with his twin sister Lauren at Camp Cambria, a summer camp for children with juvenile arthritis. Stephen began spending time with Sarah outside of camp, where he met her friends and Kaitlin. Stephen and Kaitlin were just friends for a couple years until they began dating in 2020.

Stephen and Kaitlin's first unofficial date was in June 2020, when restaurants were allowed to serve guests on patios for the first time since the COVID lockdown. Kaitlin invited a group of her friends (including Stephen) to dinner at Pat McGovern's near her apartment in St Paul. Stephen paid for Kaitlin's dinner, and they began spending time 1:1 to share wine and chat at Kaitlin's apartment about once a week. Both Kaitlin and Stephen felt something but were nervous to make a move and disrupt the friendship they had built. Kaitlin's friend Beth noticed something between them immediately and encouraged Stephen to make a move, and the rest is history! Stephen proposed to Kaitlin in Puerto Rico, their favorite vacation spot in May 2025.