Zach Bryan on the 2023 Academy of Nation Music Awards Casey Flanigan/imageSPACE/Shutterstock
Rising artist Zach Bryan‘s swoon-worthy songwriting has followers curious in regards to the real-life love tales that impressed them.
Bryan's profession took off after the 2022 launch of his album American Heartbreak, his first document with a serious label. He beforehand dropped DeAnn and Elisabeth in 2019 and 2020, respectively, later solidifying his place within the business with the viral success of his Grammy-nominated single, “One thing within the Orange.”
With a robust base of devoted followers, Bryan has gone from performing for a small TikTok viewers to filling stadiums. His private life, nonetheless, has remained comparatively below wraps — till he sparked a romance with a Barstool Sports activities persona in 2023.
Scroll right down to study extra about Bryan's love life by means of the years — together with his whirlwind marriage:
Rose Madden
The previous spouses tied the knot in July 2020, however their marriage didn't final lengthy. By July 2021, the twosome had known as it quits.
On 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 photograph.
Deb Peifer
Deb Peifer Courtesy of Deb Peifer/Instagram
Following his break up from Madden, the songwriter moved on with Peifer. The pair steadily gave followers glimpses of their life collectively — and their canine — earlier than Bryan introduced their breakup in Might 2023.
“For transparency and with respect I'm letting everybody know Debra and me went our separate methods a few week and a half in the past. Issues are mutual between us, we're leaving with a lot reminiscences and good occasions,” he tweeted. “I urge a lot that everybody respects her and my privateness by means of a tough time.”
Brianna LaPaglia
Brianna “Chickenfry” Lapaglia Courtesy of Brianna Lapaglia/Instagram
The Barstool Sports activities persona made a shock look on stage throughout certainly one of Bryan's New York Metropolis live shows in June 2023 — and courting rumors have been sparked quickly after. The pair initially crossed paths earlier that yr on the 2023 ACM Awards weeks earlier than Bryan introduced his break up from Peifer.
LaPaglia — a.okay.a. Brianna Chickenfry — addressed the duo's relationship on her “PlanBri Uncut” podcast in July 2023. “It's enjoyable, it's informal, and yeah, I simply needed to handle it as a result of the entire web is freaking the f—okay out and individuals are doing s—t,” she stated, confirming that she was seeing Bryan. “And yeah, that's actually it. Simply hanging out, having some enjoyable.”
All through the summer season, the pair spent extra time with one another, together with in Bryan's native Oklahoma. Following his September 2023 arrest for “obstruction of investigation,” LaPaglia seemingly poked enjoyable at her boyfriend's controversy by sharing Britney Spears‘ “Felony” through her Instagram Story.
After a yr of courting, Bryan introduced through his Instagram Story that he and LaPaglia have been performed. “Brianna and me have damaged up with one another and I respect and love her with each ounce of my coronary heart,” he wrote in October 2024. “She has cherished me unconditionally for a really very long time and for that I'll all the time thank her.”
The “I Bear in mind The whole lot” singer famous that he's had “an extremely onerous yr personally and struggled by means of some fairly extreme issues,” which contributed to the break up.
“I assumed it will be useful for each of us to go our alternative ways. I'm not excellent and by no means might be,” he continued. “With the whole lot I'm and to anybody I let down, I'm sorry. I attempt my finest in the whole lot. I failed folks that love me and largely myself.”
Samantha Leonard
Leonard confirmed her romance with Bryan in August 2025, sharing loved-up Instagram images from a joint boat journey.
