Zach Bryan's Dating History: From Ex-Wife Rose Madden to Ex-Girlfriends Deb Peifer and Brianna Chickenfry

Zach Bryan often sings about love, drawing inspiration from his past relationships.

The Grammy-winning singer-songwriter was married to Rose Madden from 2020 to 2021, and in relationships with Deb Peifer from 2022 to 2023 and BFFs podcast host Brianna ‘Chickenfry’ LaPaglia from 2023 to 2024.

In July 2024, LaPaglia shared on Instagram a sweet tribute to Bryan for their anniversary, writing that he “helped me love myself again.”

“A year full of loving harder than I thought I was capable of and laughing louder than any year before,” she wrote in the caption the post. “There isn’t a damn thing I wouldn’t do for ya."

However, just three months later, Bryan announced he and LaPaglia broke up, opening up about how his personal struggles have led him to “fail people” who love him.

“I have had an incredibly hard year personally and struggled through some pretty severe things. I thought it would be beneficial for both of us to go our different ways. I am not perfect and never will be,” he wrote on his Instagram Stories. “With everything I am and to anyone I let down, I am sorry. I try my best in everything. I failed people that love me and mostly myself.”

Here’s a look back at Zach Bryan’s dating history.

Rose Madden 

Madden reportedly served in the U.S. Navy with Bryan, and the two got married in 2020. In 2021, reports surfaced that the two had called it quits after less than a year of marriage.

In May 2021, Madden confirmed the split herself when she posted a TikTok video that read, “✨when your ex husband moves out, and you are now forced to cook potatoes with a f------- pumpkin pie mold✨.”

Bryan’s 2020 studio album, Elisabeth, was rumored to be named after Madden’s middle name, per Holler. The album had previously had a photo of the two of them on the cover, but it has since been changed to a black screen.

Madden also appears in the first episode of his series, The Belting Bronco, a project in which Bryan features various musical guests riding in the back of his Ford Bronco. The video opens with Madden starting the car, then transitions to Bryan singing from the back with Madden providing subtle backup vocals next to him.

“It’s something else when you love somebody and you’re singing a song about them, and then when they’re singing it with you. It’s unbelievable,” Bryan said after singing “Mine” with her on a separate occasion. “Her voice is just amazing and I love her more than anything in the world.”

Madden has since moved on with her current boyfriend, Sebastian, whom she met in 2021, according to her Instagram Stories. However, the two didn’t start hanging out until their deployment in 2022.

“I was actually dating someone else at the time we became friends, so that allowed us the opportunity to develop a beautiful friendship before ever even considering pursuing a romantic relationship with each other,” she wrote in February 2024.

“A few months later that relationship ended, and we continued to just be friends for a while, even joked that it would ‘never work’ if we tried to date hahah,” she added.

Deb Peifer

Bryan and Deb went public with their relationship in 2022. While they were together, the former couple shared bits of their relationship on social media, including a since-deleted TikTok clip of them singing Taylor Swift's “Tim McGraw” as a joking plea to receive tickets for the Eras Tour.

However, in May 2023, Bryan announced their split.

“For transparency and with respect I am letting everyone know Debra and me went our separate ways about a week and a half ago,” he wrote in an announcement on X. “Things are mutual between us, we’re leaving with plenty [of] memories and good times.”

The night before he made the announcement, he debuted the first live performance of “All the Time” — a song with lyrics reflecting a failed relationship — at his show in Philadelphia. He wrote on X once again to clarify that his decision to sing the song for the first time had nothing to do with the break-up.

“and me playing All The Time last night had actually nothing to do with my previous tweet,” he wrote. “I got hundreds of dm’s of people asking me to play it and it was about time I did it.”

That was the last time he spoke publicly about the relationship, and both Peifer and Bryan have since deleted all traces of their romance from their social media accounts. In September 2024, Peifer revealed she was in a new relationship in a TikTok video, sharing that she "was alone for a bit" before she started dating again. "Everyone has different relationships, it's okay if you take a little extra time," she wrote.

Brianna LaPaglia

Bryan and LaPaglia — who were both in separate relationships at the time — first met at the Academy of Country Music Awards in May 2023 when she asked him for a photo together, despite not saying much to each other at the event.

A month later, LaPaglia attended his New York City concert with her BFFs cohost Joshua Richards, where they both joined Bryan on stage to sing one of his songs.

But it wasn’t until Bryan “slid into [her] DMs” that the two started speaking, she revealed on BFFs.

“I made a podcast after we went onstage and was like, ‘Eat the rich besides Zach Bryan’ and he posted it and then he DM’d me and said, ‘That was so sweet, thank you guys for coming.’ And then we just started chatting,” LaPaglia said.

In July 2023, she confirmed their relationship on her podcast, PlanBri Uncut, later revealing that they had bonded during an 18-hour car ride together before making it official.

They made their red carpet debut at the Grammy Awards in February. For months, she accompanied him on the road and on stage during his Quittin' Time tour. In July 2024, Bryan marked their 1-year anniversary with an Instagram tribute, admitting, "people are annoying with stuff like this and now I understand why."

“Happy anniversary and I love you so much Brianna," he continued. "Just about one of the only people that makes me laugh anymore and OFTEN. Proud to call you my girl."

However, in October 2024, the two called it quits. Bryan confirmed the split on his Instagram Stories, writing that he thought it would be best for them to go their “separate ways.”

"Addressing something: 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," he wrote.

LaPaglia shared a statement on PlanBri Uncut in which she revealed that she felt “blindsided” by Bryan’s Instagram announcement.

"I'm at the point where it's like, how can you give someone everything and love them so unconditionally, like through stuff that you shouldn't because you just love them and you want them ... like you see the good in them?" she said while crying on her bathroom floor.