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

Country rocker Zach Bryan‘s swoon-worthy songwriting has fans curious about the real-life love stories that inspired them.

Bryan’s career took off after the 2022 release of his album American Heartbreak, his first record with a major label. He previously dropped DeAnn and Elisabeth in 2019 and 2020, respectively, later solidifying his place in the industry with the viral success of his Grammy-nominated single, “Something in the Orange.”

With a strong base of dedicated fans, Bryan has gone from performing for a small TikTok audience to filling stadiums. His personal life, however, has remained relatively under wraps — until he sparked a romance with a Barstool Sports personality in 2023.

Scroll down to learn more about Bryan’s love life through the years — including his surprise marriage to Samantha Leonard:

Rose Madden

The former spouses tied the knot in July 2020, but their marriage didn’t last long. By July 2021, the twosome had called it quits.

At the time, Madden returned to social media after a noticeable absence — and wiped all pics with Bryan from her feed. “She’s ba—ack ;-),” she captioned a solo photo.

Deb Peifer

Following his split from Madden, the songwriter moved on with Peifer. The pair frequently gave fans glimpses of their life together — and their dog — before Bryan announced their breakup in May 2023.

“For transparency and with respect I am letting everyone know Debra and me went our separate ways about a week and a half ago. Things are mutual between us, we’re leaving with plenty memories and good times,” he tweeted. “I beg so much that everyone respects her and my privacy through a hard time.”

Brianna LaPaglia

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.