We met on the very first day of eighth grade. Ben had just transferred to Freeland Middle School, and Bailey was at her locker switching out books when she noticed someone new in the hallway. Her friend caught her looking, leaned in, and whispered, “That’s the new kid… Ben Fleming.” And that’s where it all started. We had our classic middle school “relationship,” which fizzled out without a real breakup. To this day, we still joke that we’ve been dating since middle school. Life moved on, as it does. And as it turns out, all good things really do come with time. Years later, we went to junior prom together as friends, where Ben was encouraged by Bailey’s friend Kennedy to shoot his shot again. But it was senior homecoming that really shifted things—our eyes met on the dance floor, and Bailey felt an unexpected wave of jealousy toward the girl Ben was dancing with. That moment cracked the door open again. Since then, we’ve been through a lot together: attending colleges in different cities, surviving COVID lockdowns, living in different states, launching our careers, navigating Bailey’s graduate school, and eventually settling into our DINK (Dual Income, No Kids) life in Milwaukee. It’s been a long story—and the best one we could’ve written together. Ben got down on one knee in our current apartment (impeccable form—you could tell he practiced) on 10/3/25. It felt fitting, as it’s the place where we cook, dance, laugh, sing, and celebrate together. He somehow managed to surprise Bailey despite their long-term relationship and even captured the moment on video. Through her uncontrolled happy sobbing, he professed his love and intentions, produced eight red roses representing the eight years we’ve been dating, and presented Volume I of The Bailey & Ben Chronicles in photo format. God bless waterproof mascara. We have decided to tie the knot exactly one year from our engagement date in our hometown of Freeland, MI.