In late April of 2024, Fil walked up to Bailley while she was sipping on a Malibu Pineapple and attending the Golf Bar Crawl at The Loft. He was in town for the PBR rodeo that was also happening that Saturday night. His hat sat slightly crooked on his head, and when Bailley reached up to fix it, Fil just grinned and said he wore it that way on purpose — probably hoping she’d keep finding reasons to touch it (and him) all night. What started as a simple adjustment turned into a sweet little excuse to stay close. The rest of the night was a blur of dancing, laughing, sidewalk twirls, and bar-hopping adventures.
Ever since that night, they have been inseparable—except for the fact that she lived in Grand Forks, North Dakota, and he lived in Winnipeg, Manitoba. Fil came down to celebrate Bailley graduating from college, Bailley went up to meet Fil's friends. Back and forth back and forth they went from Grand Forks to Winnipeg to see each other.
Two months later, Fil asked Bailley a question: “The next time I cross the border, should I tell border patrol I’m going to see my girlfriend?”
Many, many trips later, the couple decided they wanted to go see Montana and the mountains of Yellowstone one fateful weekend in early November of 2025. Driving through the winding Yellowstone scenery, they pulled over at one of the many scenic outlook spots along their route. As Bailley stood on top of a large rock, looking out over the small creek and the mountains beyond, she heard Fil say, “Turn around.” As she did, she saw Fil on one knee, tears in his eyes, as he asked, “Will you marry me?”
And she said yes.