Zach Bryan is one of the fastest-rising stars in American country music, who is known for his raw, storytelling style and heartfelt songwriting. Born in Okinawa, Japan, to a military family and raised in Oologah, Oklahoma, Bryan served in the U.S. Navy for eight years before turning to music full-time. His songs, have earned him a devoted fan base and critical acclaim both alike.
Bryan’s breakthrough came with his independently released albums DeAnn (2019) and Elisabeth (2020), both recorded with a minimalist setup that highlighted his powerful lyrics and raspy, unfiltered vocals. However, it was his 2022 album, American Heartbreak, his first album with a major label, that shot him to stardom. The album’s massive success, and the Grammy-nominated single, Something in the Orange, cemented him as one of the most authentic voices in modern country music.
Despite his soaring career, Bryan’s personal life has been anything but smooth. His relationships have often been inspiration behind his music and have been marked by deep emotions, heartbreak, and public scrutiny. Here’s a closer look at Zach Bryan’s dating history, from his early marriage to his most recent romance.
Rose Madden, Zach Bryan’s ex-wife, who inspired his early music
Zach Bryan married Rose Madden in July 2020, during the early stages of his career when he was still rising to fame. Their love story seemed like something out of his own songs, simple, heartfelt, and full of promise. However, their marriage was short-lived. Within a year, by July 2021, the two had quietly split, surprising fans who had followed their relationship online.
Following the separation, Rose returned to social media after a long absence, posting a solo photo with the caption, “She’s ba—ack ;-)”, and wiped all photos of Bryan from her profile. The move subtly confirmed the breakup, even thought neither of them addressed the reasons behind it. While Bryan rarely speaks about his past relationships publicly, fans have speculated that several of his early songs particularly on DeAnn and Elisabeth, drew inspiration from his marriage.
Zach Bryan and his relationship with Deb Peifer
After his split from Madden, Bryan found love again with Deb Peifer, a social media manager and influencer. The couple frequently shared glimpses of their everyday life together, often accompanied by their beloved dog. However, in May 2023, Bryan took to Twitter to announce their breakup. The breakup appeared amicable, and Peifer did not make any public comment about it. Fans praised Bryan for his transparency and respectful handling of the situation. He wrote:
“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. I beg so much that everyone respects her and my privacy through a hard time.”
Brianna LaPaglia and Zach Bryan’s romance made headlines
Not long after his split from Peifer, Bryan’s love life made headlines again, this time, he was linked to Brianna LaPaglia, better known as Brianna Chickenfry, a popular Barstool Sports personality and podcast host. The two first crossed paths at the 2023 Academy of Country Music Awards, weeks before Bryan publicly confirmed his split from Peifer.
Their chemistry became apparent when Brianna made a surprise appearance on stage during one of Bryan’s New York concerts in June 2023, sparking widespread dating rumours. Brianna confirmed their relationship on her PlanBri Uncut podcast in July 2023, saying:
“It’s fun, it’s casual, and yeah, I just wanted to address it because the whole internet is freaking the f—k out… Just hanging out, having some fun.”
Throughout the summer, the couple spent more time together, often in Bryan’s home state of Oklahoma. However, their relationship also weathered controversy, particularly after Bryan’s September 2023 arrest for obstruction of investigation. In a cheeky social media moment, Brianna shared Britney Spears’ song Criminal on her Instagram Story, seemingly poking fun at the situation. After a year of dating, Bryan announced their breakup in October 2024 via Instagram Story. He wrote:
“Brianna and me have broken up with each other and I respect and love her with every ounce of my heart. She has loved me unconditionally for a very long time and for that I’ll always thank her.”
Bryan went on to describe the personal struggles he faced during the year, saying he thought it would be beneficial for both of them to go their different ways. He admitted he was not perfect and never will be. He had failed those who loved him, and mostly, he had failed himself. There were speculations of cheating being the reason behind their breakup and Brianna had caught Bryan using the celebrity dating app, Raya.
Zach Bryan and Samantha Leonard have been dating for a while now
After months of speculation, Bryan seemed to have found love again and this time with Samantha Leonard. The two were first linked in August 2025, when Leonard shared romantic photos from a boat trip on Instagram, confirming their relationship. The posts showed the pair laughing and embracing, suggesting a fresh start for the I Remember Everything singer after a turbulent few years.
While little is known about Leonard, her social media presence hints at the couple’s shared love for travel, music, and the outdoors. Fans have reacted positively to the new romance, hoping that Bryan’s latest relationship will bring him peace and happiness after a series of emotional ups and downs.
Zach Bryan’s love life has mirrored his music. Whether it’s heartbreak, healing, or new beginnings, his relationships have shaped not only his personal journey but also his career. Each chapter, from Rose Madden to Samantha Leonard, reflects a different era in his life and often finds a place in his heartfelt lyrics.
Despite public scrutiny and personal struggles, Zach Bryan continues to pour his emotions into his music and it has made him one of country music’s most relatable voices.
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