Zach Bryan and Ex-Girlfriend Deb Peifer’s Relationship Timeline

Jason Kempin/Getty Images ; Courtesy of Deb Peifer/Instagram

Zach Bryan’s dating history has come under some scrutiny following his breakup from Brianna “Chickenfry” LaPaglia, with fans looking specifically into his relationship with ex-girlfriend Deb Peifer.

Bryan took this relationship with Peifer public in early 2022, months after his marriage to Rose Madden came to an end. The couple shared glimpses into their relationship during their time together, which came to an end in May 2023. (Bryan moved on with LaPaglia shortly thereafter.)

After their breakup, Peifer seemed to stay quiet about what went wrong with the country star. LaPaglia — who split from the singer in October 2024 — has since alluded to his exes keeping their mouth shut for a certain reason.

LaPaglia alleged in a November 2024 podcast episode that she was offered a hefty sum of $12 million to sign an NDA regarding her experiences dating Bryan. The Barstool Sports podcast host referenced “the people before” when discussing the alleged offer on her podcast episode.

“You made the women before me believe that they had no other choice to take money from you, sign their experiences away, sign what they went through away,” LaPaglia claimed. While Peifer has not addressed any of LaPaglia’s comments, she did post a TikTok video dancing to Taylor Swift’s “Clean” — which some fans have taken as a response.

Keep scrolling to look back on Bryan’s relationship with Peifer:

January 2022

Bryan and Peifer made their relationship Instagram official.

September 2022

Courtesy of Deb Peifer/Instagram

During their relationship, Bryan did a rare interview with The New York Times and Peifer was even quoted in the profile.

“Sometimes he’s so levelheaded that I’m like, ‘Wait, you should be mad or something.’ Like, we need to react to this!” she said of Bryan’s level of emotions at the time.

She also spoke candidly about Bryan’s reaction to fame.

“He had like a week and a half off,” Peifer recalled. “Got back, recorded some songs, and then took four days to build cabinets. And it was all of the exact same importance.”

September 2022

That same month, Peifer shared a photo of her kissing Bryan on Instagram.

October 2022

Courtesy of Zach Bryan/Instagram

Peifer remains in an image on Bryan’s Instagram in which he was celebrating a major milestone for his song “Something in the Orange.” Her hand is resting on his chest in the group photo.

March 2023

Bryan was featured in a video that’s still on Peifer’s Instagram, despite most of their past posts having been removed. “A lot going on in here, mostly pickles though,” the caption read.

May 2023

Bryan confirmed via social media that he and Peifer had 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. Things are mutual between us, we’re leaving with plenty memories and good times,” his statement read. “I beg so much that everyone respects her and my privacy through a hard time.”