:max_bytes(150000):strip_icc():focal(999x0:1001x2)/ZachBryanDatingHistorySPLIT-70066c0d51c14f439e54236d3612e533.jpg)
So, you’re scrolling through TikTok or checking your Spotify wrapped and you realize Zach Bryan isn’t just making music about heartbreak anymore—he’s actually living a whole new chapter. Honestly, keeping up with who Zach Bryan is dating has felt like a full-time job for country fans over the last couple of years. One minute he’s with a Barstool star, the next there are rumors of $12 million NDAs, and then suddenly, he’s posting photos from a wedding in Spain.
If you’ve been out of the loop, the short answer is: he’s not "dating" anymore. He’s married.
Zach Bryan officially tied the knot with Samantha Leonard on New Year’s Eve, 2025. It wasn't some massive Nashville blowout with a red carpet and a thousand influencers. Instead, they eloped—or at least kept it very tight-knit—at the Basílica de Santa María del Coro in San Sebastián, Spain.
Who exactly is Samantha Leonard?
People have been digging to find out who this woman is because she seemingly appeared out of nowhere right as the dust was settling from his messy split with Brianna "Chickenfry" LaPaglia. Samantha isn't a public figure in the way his exes were. She’s a California native, an NYU grad, and from what we can tell through the social media breadcrumbs, she’s a massive adrenaline junkie.
Zach’s birthday tribute to her back in October 2025 basically told us everything we needed to know. He mentioned her hiking six miles in Chanel flats and skydiving over the Alps. That's a vibe.
💡 You might also like: What Really Happened With Dane Witherspoon: His Life and Passing Explained
Their relationship moved fast. Like, really fast. They were first spotted together around July 2025 at the Running of the Bulls in Spain. By December, they were saying "I do" in that same country. Some fans have pointed out that she bears a striking resemblance to his ex-girlfriend Brianna, which sparked a whole "he has a type" discourse on Reddit, but the couple seems to be ignoring the noise.
The messy road to the altar
You can't really talk about who Zach Bryan is dating now without acknowledging the absolute chaos of late 2024. His breakup with Brianna Chickenfry was a disaster. There’s no other way to put it.
After they split in October 2024, Brianna went on her podcast, BFFs, and dropped some serious bombs. She alleged that Zach’s team offered her a staggering $12 million to sign an NDA and never talk about their relationship. She turned it down. She also spoke about emotional abuse and "walking on eggshells," which changed the way a lot of people viewed the "Something in the Orange" singer.
Then came the music. Zach’s 2026 album, With Heaven on Top, is basically a roadmap of his transition from that "toxic" era to his life with Samantha.
📖 Related: Why Taylor Swift People Mag Covers Actually Define Her Career Eras
- The Song "Skin": This one has fans losing their minds. He sings about taking a blade to his old tattoos to "drain the blood between me and you." It’s a pretty clear shot at the matching "How lucky are we" tattoos he had with Brianna.
- The Song "Runny Eggs": A much softer track that fans believe is a love letter to Samantha and their quieter life together.
Why this relationship feels different
A lot of people are skeptical. They look at his track record—a marriage to Rose Madden that ended in 2021, a long-term relationship with Deb Peifer, and the Brianna saga—and wonder if this one will stick.
But Zach has been vocal about being in therapy and trying to "heal." On his Instagram, he mentioned that conversations about the future and "Sammy’s happiness" made him change his priorities. He even shared a detail that had fans tearing up: Samantha had lace from Zach’s late mother’s wedding dress sewn into her own gown. For a guy who has built his entire career on the memory of his mom, DeAnn, that’s a heavy gesture.
What you should know about Zach’s dating history
If you're trying to keep the timeline straight, here is the basic flow of how we got here:
- Rose Madden: The OG wife. They married in 2020 while he was still in the Navy and divorced about a year later.
- Deb Peifer: The relationship that spanned his massive rise to fame. They split in May 2023.
- Brianna LaPaglia: The high-profile, high-drama era. July 2023 to October 2024.
- Samantha Leonard: The current chapter. Started dating mid-2025, married December 31, 2025.
Is he finally settled? Only time will tell, but for now, the "dating" rumors are officially dead because he's a married man again. He seems to be leaning into a more private, international lifestyle, far away from the Barstool drama and the New York City paparazzi.
👉 See also: Does Emmanuel Macron Have Children? The Real Story of the French President’s Family Life
If you’re a fan, the best way to keep up with them isn't through the tabloids—it's through the lyrics. Zach has always processed his love life in real-time through his songwriting. If things are good with Samantha, expect the next few EPs to be a lot more "heaven" and a lot less "orange."
Keep an eye on his tour dates for 2026. Samantha has been spotted at almost every show since they went public, often hanging out with Zach's sister. It looks like she’s integrated into the family, which is usually a big sign for Zach that things are serious.
Just don't expect another public breakup video any time soon. If this marriage is as "tougher than the rest" as he says it is, he might finally be off the market for good.