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Singer Zach Bryan’s Dating History: From Ex-Wife to Barstool Fling

Zach Bryan Dating History
Zach Bryan at the 2023 Academy of Country Music Awards Casey Flanigan/imageSPACE/Shutterstock

Rising artist 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 whirlwind marriage:

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.

Zach Bryan Dating History
Deb Peifer Courtesy of Deb Peifer/Instagram

“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.

Zach Bryan Dating History
Brianna “Chickenfry” Lapaglia Courtesy of Brianna Lapaglia/Instagram

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.