Zach Bryan at the 2023 Academy of Country Music Awards
Casey Flanigan/imageSPACE/ShutterstockCountry rocker Zach BryanThe swoon-worthy songwriting has fans curious real life love stories that inspired them.
Bryan’s career took off after the 2022 release his album American Heartbreakhis first record with a major label. It fell before DeAnn i Elizabeth 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 small TikTok audiences to filling stadiums. His personal life, however, has remained relatively secret, until he sparked a romance with a Barstool Sports personality in 2023.
Scroll down to learn more about Bryan’s love life over the years, including his surprise marriage a Samantha Leonard:
Rose Madden
The former spouses tied the knot in July 2020, but their marriage was short-lived. By July 2021, the two had called it quits.
Madden then returned to social media after a notable absence and deleted all photos with Bryan from her feed. “She’s ba-ack ;-),” she subtitled a solo photo.
Deb Peifer
Deb Peifer
Courtesy of Deb Peifer/InstagramAfter his split from Madden, the composer continued with Peifer. The couple often gave fans a glimpse of their life together, and their dog, before Bryan announced their split in May 2023.
“Out of transparency and respect, I’m letting everyone know that Debra and I broke up about a week and a half ago. Things are mutual between us, we’re leaving with lots of memories and good times,” he tweeted. “I pray so much that everyone respects her and my privacy in this difficult time.”
Brianna LaPaglia
Brianna “Chickenfry” Lapaglia
Courtesy of Brianna Lapaglia/InstagramBarstool’s sports personality made a surprise appearance on stage during one of Bryan’s concerts in New York in June 2023, and dating rumors followed soon after. The pair initially crossed paths earlier that year in the 2023 ACM Awards weeks before Bryan announced his split from Peifer.
LaPaglia, aka Brianna Chickenfry, addressed the duo’s relationship on her “PlanBri Uncut” podcast in July 2023. “It’s funny, it’s casual, and yeah, I just wanted to address it because the whole internet is bullshitting and people are bullshitting,” she said, confirming that she was like Bryan. “And yes, that’s really it. Just hanging out, having fun.”
Throughout the summer, the couple spent more time with each other, even in Bryan’s native Oklahoma. After her arrest in September 2023 for “obstructing an investigation,” LaPaglia apparently poked fun at her boyfriend’s controversy by sharing Britney Spears“Criminal” via his Instagram story.
After a year of dating, Bryan announced it via his Instagram story he and LaPaglia were done. “Brianna and I have broken up and I respect and love her with all my heart,” he wrote in October 2024. “She has loved me unconditionally for a long time and for that I will always be grateful.”
The “I Remember Everything” singer noted that he’s had “an incredibly tough year personally and has been struggling with some really serious things,” which contributed to the split.
“I thought it would be beneficial for both of us to go our separate ways. I’m not perfect and I never will be,” he continued. “With everything I am and anyone I disappoint, I’m sorry. I do my best in everything. I failed the people who love me and especially myself.”
Zach Bryan is officially off the market after marrying Samantha Leonard. The country singer ended 2025 saying “I do” to Leonard in an intimate wedding celebration in Spain. “Harder than the rest,” Bryan wrote via Instagram on New Year’s Eve, with a first look at the couple’s wedding day look. According to (…)
Samantha Leonard
Leonard confirmed his romance with Bryan in August 2025, sharing his love for him Instagram photos of a joint boat trip.
Bryan went Official Instagram with Leonard two months later when he was celebrating his birthday.
“To the only woman who can walk six miles in Chanel flats, skydive over the Alps and catch a fish bigger than me all in the same day,” she wrote in October 2025. “I hope your day was as stylish as you are.”
In December 2025, Bryan confirmed that she married Leonard during a private wedding ceremony in Spain. “Harder than the rest,” he wrote Instagram on the last day of 2025 with a first look at the couple’s wedding dress.