Zach Bryan's Romantic Journey: From Past Flames to Current Marriage

Rising country star Zach Bryan’s heartfelt songwriting has captivated listeners and sparked curiosity about the real-life romances that inspire them.

Bryan’s career gained significant momentum following the 2022 release of his album American Heartbreak, his debut record with a major label. He previously released DeAnn and Elisabeth in 2019 and 2020, respectively, later solidifying his position in the music industry with the widespread popularity of his Grammy-nominated single, “Something in the Orange.”

With a devoted fanbase, Bryan has transitioned from performing for a small TikTok audience to headlining large venues. His personal life, however, has largely remained private – until he began a relationship with a Barstool Sports personality in 2023.

Continue reading to discover more about Bryan’s romantic history through the years – including his unexpected marriage to Samantha Leonard:

Rose Madden

The former partners exchanged vows in July 2020, but their marriage was short-lived. By July 2021, the couple had decided to separate.

At the time, Madden returned to social media after a period of absence – and removed all photographs featuring Bryan from her profile. “She’s back ;-),” she captioned a solo image.

Deb Peifer

After his split from Madden, the songwriter began dating Peifer. The pair often shared glimpses of their life together – and their dog – before Bryan announced their breakup in May 2023.

“For clarity and out of respect, I want to let everyone know that Debra and I have gone our separate ways about a week and a half ago. Our decision is mutual, and we are parting with many cherished memories and good times,” he shared on Twitter. “I kindly request that everyone respect her and my privacy during a difficult 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 quickly emerged. The pair initially met earlier that year at the 2023 ACM Awards, weeks before Bryan announced his separation from Peifer.

LaPaglia – also known as Brianna Chickenfry – addressed the couple’s relationship on her “PlanBri Uncut” podcast in July 2023. “It’s enjoyable, it’s casual, and yes, I wanted to address it because the entire internet is reacting strongly and people are behaving inappropriately,” she stated, confirming that she was dating Bryan. “And that’s essentially it. Just spending time together and having fun.”

Throughout the summer, the pair spent more time together, including in Bryan’s home state of Oklahoma. Following his September 2023 arrest for “obstruction of investigation,” LaPaglia seemingly playfully referenced her boyfriend’s legal issue by posting Britney Spears’ “Criminal” to her Instagram Story.

After a year of dating, Bryan announced via his Instagram Story that he and LaPaglia had ended their relationship. “Brianna and I have decided to go our separate ways, and I cherish and love her with all my heart,” he wrote in October 2024. “She has loved me unconditionally for a considerable amount of time, and for that, I will always be grateful to her.”

The “I Remember Everything” singer noted that he’s experienced “an incredibly challenging year personally and struggled through some quite difficult situations,” which contributed to the breakup.

“I am not flawless and never will be,” he continued. “With everything I am and to anyone I may have disappointed, I am truly sorry. I strive to do my best in all aspects of my life. I have let down those who care about me and, most importantly, myself.”

Who Is Samantha Leonard? What to Know About Zach Bryan’s Wife

Samantha Leonard

Leonard confirmed her romance with Bryan in August 2025, sharing affectionate Instagram photos from a joint boat excursion.

Bryan publicly acknowledged his relationship with Leonard two months later while celebrating her birthday.

“To the only woman who can wear six-mile Chanel flats, skydive over the Alps, and reel in a bigger fish than me all in the same day,” he wrote in October 2025. “Wishing you a day 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, sharing a first look at the couple’s wedding attire.