Singer Zach Bryan’s Dating History: From Barstool Sports’ Brianna LaPaglia to Samantha Leonard

The Barstool Sports personality made a surprise appearance on stage during one of Bryan’s New York City concerts in June 2023 — and dating rumors were sparked soon after. The pair initially crossed paths earlier that year at the 2023 ACM Awards weeks before Bryan announced his split from Peifer.

LaPaglia — a.k.a. Brianna Chickenfry — addressed the duo’s relationship on her “PlanBri Uncut” podcast in July 2023. “It’s fun, it’s casual, and yeah, I just wanted to address it because the whole internet is freaking the f—k out and people are doing s—t,” she said, confirming that she was seeing Bryan. “And yeah, that’s really it. Just hanging out, having some fun.”

Throughout the summer, the pair spent more time with each other, including in Bryan’s native Oklahoma. Following his September 2023 arrest for “obstruction of investigation,” LaPaglia seemingly poked fun at her boyfriend’s controversy by sharing Britney Spears‘ “Criminal” via her Instagram Story.

After a year of dating, Bryan announced via his Instagram Story that he and LaPaglia were done. “Brianna and me have broken up with each other and I respect and love her with every ounce of my heart,” he wrote in October 2024. “She has loved me unconditionally for a very long time and for that I’ll always thank her.”

The “I Remember Everything” singer noted that he’s had “an incredibly hard year personally and struggled through some pretty severe things,” which contributed to the split.

“I thought it would be beneficial for both of us to go our different ways. I am not perfect and never will be,” he continued. “With everything I am and to anyone I let down, I am sorry. I try my best in everything. I failed people that love me and mostly myself.”

Samantha Leonard

Leonard confirmed her romance with Bryan in August 2025, sharing loved-up Instagram photos from a joint boat trip.

Bryan went Instagram official with Leonard two months later when celebrating her birthday.

“To the only woman who can hike six miles in Chanel flats, skydive over the alps and catch a bigger fish than me all in the same day,” he wrote in October 2025. “Hope your day was as graceful as you are.”

In December 2025, Bryan confirmed he married Leonard during a private wedding ceremony in Spain. “Tougher than the rest,” he wrote via Instagram on the final day of 2025 with a first look at the couple’s wedding attire.