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Singer Zach Bryan’s Dating History: From Ex-Wife to Barstool Fling on September 13, 2023 at 4:44 pm Us Weekly

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Zach Bryan at the 2023 Academy of Country Music Awards Casey Flanigan/imageSPACE/Shutterstock

Rising artist Zach Bryan‘s swoon-worthy songwriting has fans curious about the real-life love stories that inspired them.

Bryan’s career took off after the 2022 release of his album American Heartbreak, his first record with a major label. He previously dropped DeAnn and Elisabeth 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 a small TikTok audience to filling stadiums. His personal life, however, has remained relatively under wraps — until he sparked a romance with a Barstool Sports personality in 2023.

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Scroll down to learn more about Bryan’s love life through the years — including his whirlwind marriage:

Rose Madden

The former spouses tied the knot in July 2020, but their marriage didn’t last long. By July 2021, the twosome had called it quits.

At the time, Madden returned to social media after a noticeable absence — and wiped all pics with Bryan from her feed. “She’s ba—ack ;-),” she captioned a solo photo.

Deb Peifer

Following his split from Madden, the songwriter moved on with Peifer. The pair frequently gave fans glimpses of their life together — and their dog — before Bryan announced their breakup in May 2023.

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Deb Peifer Courtesy of Deb Peifer/Instagram

“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,” he tweeted. “I beg so much that everyone respects her and my privacy through a hard 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 were sparked soon after. The pair initially crossed paths earlier that year at the 2023 ACM Awards weeks before Bryan announced his split from Peifer.

Brianna “Chickenfry” Lapaglia Courtesy of Brianna Lapaglia/Instagram

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LaPaglia — a.k.a. Brianna Chickenfry — addressed the duo’s relationship on her “PlanBri Uncut” podcast in July 2023. “It’s fun, it’s casual, and yeah, I just wanted to address it because the whole internet is freaking the f—k out and people are doing s—t,” she said, confirming that she was seeing Bryan. “And yeah, that’s really it. Just hanging out, having some fun.”

Throughout the summer, the pair spent more time with each other, including in Bryan’s native Oklahoma. Following his September 2023 arrest for “obstruction of investigation,” LaPaglia seemingly poked fun at her boyfriend’s controversy by sharing Britney Spears‘ “Criminal” via her Instagram Story.

Rising artist Zach Bryan‘s swoon-worthy songwriting has fans curious about the real-life love stories that inspired them. Bryan’s career took off after the 2022 release of his album American Heartbreak, his first record with a major label. He previously dropped DeAnn and Elisabeth in 2019 and 2020, respectively, later solidifying his place in the industry 

​   Us Weekly Read More 

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What We Can Learn Inside 50 Cent’s Explosive Diddy Documentary: 5 Reasons You Should Watch

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50 Cent’s new Netflix docuseries about Sean “Diddy” Combs is more than a headline-grabbing exposé; it is a meticulous breakdown of how power, celebrity, and silence can collide in the entertainment industry.

Across its episodes, the series traces Diddy’s rise, the allegations that followed him for years, and the shocking footage and testimonies now forcing a wider cultural reckoning.

For viewers, it offers not just drama, but lessons about media literacy, accountability, and how society treats survivors when a superstar is involved.

Rapper 50 Cent pictured in Tup Tup Palace night club with owners James Jukes and Matt LoveDough, Newcastle, UK, 7th November 2015

1. It Chronicles Diddy’s Rise and Fall – And How Power Warps Reality

The docuseries follows Combs from hitmaker and business icon to a figure facing serious criminal conviction and public disgrace, mapping out decades of influence, branding, and behind-the-scenes behavior. Watching that arc shows how money, fame, and industry relationships can shield someone from scrutiny and delay accountability, even as disturbing accusations accumulate.

Rapper 50 Cent pictured in Tup Tup Palace night club with owners James Jukes and Matt LoveDough, Newcastle, UK, 7th November 2015

2. Never-Before-Seen Footage Shows How Narratives Are Managed

Exclusive footage of Diddy in private settings and in the tense days around his legal troubles reveals how carefully celebrity narratives are shaped, even in crisis.

Viewers can learn to question polished statements and recognize that what looks spontaneous in public is often the result of strategy, damage control, and legal calculation.

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3. Survivors’ Stories Highlight Patterns of Abuse and Silence

Interviews with alleged victims, former staff, and industry insiders describe patterns of control, fear, and emotional or physical harm that were long whispered about but rarely aired in this detail. Their stories underline how difficult it is to speak out against a powerful figure, teaching viewers why many survivors delay disclosure and why consistent patterns across multiple accounts matter.

4. 50 Cent’s Approach Shows Storytelling as a Tool for Accountability

As executive producer, 50 Cent uses his reputation and platform to push a project that leans into uncomfortable truths rather than protecting industry relationships. The series demonstrates how documentary storytelling can challenge established power structures, elevate marginalized voices, and pressure institutions to respond when traditional systems have failed.

5. The Cultural Backlash Reveals How Society Handles Celebrity Accountability

Reactions to the doc—ranging from people calling it necessary and brave to others dismissing it as a vendetta or smear campaign—expose how emotionally invested audiences can be in defending or condemning a famous figure. Watching that debate unfold helps viewers see how fandom, nostalgia, and bias influence who is believed, and why conversations about “cancel culture” often mask deeper questions about justice and who is considered too powerful to fall.

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South Park’s Christmas Episode Delivers the Antichrist

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A new Christmas-themed episode of South Park is scheduled to air with a central plot in which Satan is depicted as preparing for the birth of an Antichrist figure. The premise extends a season-long narrative arc that has involved Satan, Donald Trump, and apocalyptic rhetoric, positioning this holiday episode as a culmination of those storylines rather than a stand‑alone concept.

Episode premise and season context

According to published synopses and entertainment coverage, the episode frames the Antichrist as part of a fictional storyline that blends religious symbolism with commentary on politics, media, and cultural fear. This follows earlier Season 28 episodes that introduced ideas about Trump fathering an Antichrist child and tech billionaire Peter Thiel obsessing over prophecy and end‑times narratives. The Christmas setting is presented as a contrast to the darker themes, reflecting the series’ pattern of pairing holiday imagery with controversial subject matter.

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Public and political reactions

Coverage notes that some figures connected to Donald Trump’s political orbit have criticized the season’s portrayal of Trump and his allies, describing the show as relying on shock tactics rather than substantive critique. Commentators highlight that these objections are directed more at the depiction of real political figures and the show’s tone than at the specific theology of the Antichrist storyline.

At the time of reporting, there have not been widely reported, detailed statements from major religious leaders focused solely on this Christmas episode, though religion-focused criticism of South Park in general has a long history.

Media and cultural commentary

Entertainment outlets such as The Hollywood Reporter, Entertainment Weekly, Forbes, Slate, and USA Today describe the Antichrist arc as part of South Park’s ongoing use of Trump-era and tech-world politics as material for satire.

These reports emphasize that the show’s treatment of the Antichrist, Satan, and prophecy is designed as exaggerated commentary rather than doctrinal argument, while also acknowledging that many viewers may see the storyline as offensive or excessive.

Viewer guidance and content advisory

South Park is rated TV‑MA and is intended for adult audiences due to strong language, explicit themes, and frequent use of religious and political satire. Viewers who are sensitive to depictions of Satan, the Antichrist, or parodies involving real political figures may find this episode particularly objectionable, while others may view it as consistent with the show’s long‑running approach to controversial topics. As with previous episodes, individual responses are likely to vary widely, and the episode is best understood as part of an ongoing satirical series rather than a factual or theological statement.

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Sydney Sweeney Finally Confronts the Plastic Surgery Rumors

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Sydney Sweeney has decided she is finished watching strangers on the internet treat her face like a forensic project. After years of side‑by‑side screenshots, “then vs now” TikToks, and long comment threads wondering what work she has supposedly had done, the actor is now addressing the plastic surgery rumors directly—and using them to say something larger about how women are looked at in Hollywood and online.

Sweeney at the 2025 Toronto International Film Festival red carpet premiere of Christy

Growing Up on Camera vs. “Before and After” Culture

Sweeney points out that people are often mistaking normal changes for procedures: she grew up on camera, her roles now come with big‑budget glam teams, and her body has shifted as she has trained, aged, and worked nonstop. Yet every new red‑carpet photo gets folded into a narrative that assumes surgeons, not time, are responsible. Rather than walking through a checklist of what is “real,” she emphasizes how bizarre it is that internet detectives comb through pores, noses, and jawlines as if they are owed an explanation for every contour of a woman’s face.

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The Real Problem Isn’t Her Face

By speaking up, Sweeney is redirecting the conversation away from her features and toward the culture that obsesses over them.

She argues that the real issue isn’t whether an actress has had work done, but why audiences feel so entitled to dissect her body as public property in the first place.

For her, the constant speculation is less about curiosity and more about control—another way to tell women what they should look like and punish them when they do not fit. In calling out that dynamic, Sweeney isn’t just defending herself; she is forcing fans and followers to ask why tearing apart someone else’s appearance has become such a popular form of entertainment.


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