7 Shocking Ways Nessa Barrett And Josh Richards Moved On From The TikTok 'Love Square' Drama (2025 Update)

The story of Nessa Barrett and Josh Richards is arguably the most defining relationship saga of the original TikTok era, a whirlwind romance known to fans as "Jessa" that ended in a dramatic explosion of social media controversy. Even as of late 2025, the curiosity surrounding the former power couple persists, fueled by lingering breakup rumors and a complicated "TikTok love square" involving their friends. While their romantic chapter closed years ago, both stars have undergone massive, transformative career shifts—Nessa into a major alt-pop artist and Josh into a formidable business mogul—proving the real drama is often found in the aftermath of a public split.

This deep dive provides the most current update on their individual lives, breaking down the infamous relationship timeline, the central figures in the drama, and how they’ve leveraged their initial fame into two completely separate, highly successful, and powerful empires in the current date of December 2025.

Nessa Barrett and Josh Richards: The Complete Biographical Profile

The former "Jessa" duo rose to prominence as foundational members of the TikTok creator scene, but their paths have significantly diverged in recent years.

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Nessa Barrett (Janesa Jaida Barrett)

• Born: August 6, 2002 (Age 23 in 2025)
• Hometown: Galloway, New Jersey
• Career Focus: Singer-Songwriter (Alt-Pop/Pop-Punk) and Social Media Personality
• Key Achievements (2025): Released the successful album AFTERCARE, completed a major headline world tour, and released a live album, AFTERCARE TOUR (LIVE IN LOS ANGELES). She has been an outspoken advocate for mental health, specifically discussing her journey with Borderline Personality Disorder (BPD).
• Notable Works: Songs like "Pain," "I Hope Ur Miserable Until Ur Dead," and the album Aftercare.

Josh Richards

• Born: January 31, 2002 (Age 23 in 2025)
• Hometown: Toronto, Canada
• Career Focus: Entrepreneur, Venture Capitalist, Podcast Host, and Media Personality
• Key Achievements (2025): Estimated net worth of $30M+. Co-founder of the $15M venture capital fund Animal Capital with partners like Noah Beck and Griffin Johnson. Co-host of the highly popular BFFs Podcast with Dave Portnoy and Brianna Chickenfry. Co-founder of the energy drink Ani Energy and a partner at the talent agency TalentX. He has been a featured speaker at major business events like Advertising Week NY 2025.
• Notable Ventures: Animal Capital, BFFs Podcast, Ani Energy, TalentX.

The Infamous 'Jessa' Relationship Timeline and Breakup Drama

The relationship between Nessa Barrett and Josh Richards, dubbed "Jessa," was a cornerstone of the Sway House era of TikTok, capturing the attention of millions of followers. Their split, however, spiraled into one of the platform's most discussed and complex scandals, often referred to as the "TikTok love square."

Timeline of the Romance and Fallout

• Late 2019: Nessa and Josh are first linked, beginning their relationship.
• January 2020: The couple makes their relationship Instagram official.
• June 2020: Nessa and Josh announce their breakup via a YouTube video, stating it was a mutual decision and they would remain friends.
• The Immediate Aftermath: The 'mutual' narrative quickly dissolved. Rumors began circulating, most notably suggesting Nessa had cheated on Josh with fellow creator Chase Hudson (Huddy), who was dating Charli D'Amelio at the time. This alleged betrayal was seen as a violation of "bro code" in the creator community.
• The Love Square Forms: The drama intensified when Nessa began dating Josh's close friend, Jaden Hossler (Jxdn), who had just broken up with his girlfriend, Mads Lewis. This overlapping timeline and the friend-to-ex-to-new-partner dynamic created the "TikTok love square" that dominated social media for months.
• Mads Lewis Speaks Out: Mads Lewis, the other party in the square, appeared on the Call Her Daddy podcast to discuss her side of the breakup with Jaden, adding significant fuel to the public fire.

While the initial breakup was framed as amicable, the subsequent relationships and public commentary revealed deep fractures. Josh Richards, on his BFFs Podcast, eventually addressed the situation, maintaining a relatively neutral stance on Nessa and Jaden's relationship, though the hurt was palpable to fans. He later definitively stated that he and Nessa would "never" get back together, effectively closing the door on any reconciliation rumors, even years later.

7 Ways Nessa and Josh Transformed Their Careers Post-Breakup

The most compelling part of the "Jessa" story is not the breakup itself, but how both individuals used the intense public scrutiny as a launchpad for highly successful, yet completely different, career paths. Their current status in 2025 shows a remarkable pivot from traditional influencer life.

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1. Nessa's Pivot to Alt-Pop Authenticity

Nessa leveraged her emotional turmoil and mental health struggles into raw, relatable music. Her album AFTERCARE, released in 2025, is a deep dive into complex emotions surrounding sex, love, obsession, and heartbreak. This pivot solidified her as a genuine artist, distancing her from the "TikToker" label and giving her topical authority in the alt-pop scene. She is currently touring, proving her music career is her primary focus.

2. Josh's Rise as a Venture Capital Mogul

Josh, unlike many of his peers, transitioned from content creation to serious business. He co-founded Animal Capital, a $15 million venture fund focused on investing in Gen Z-centric startups. This move established him as a legitimate entrepreneur in the finance world, working alongside former Goldman Sachs bankers.

3. The Power of the BFFs Podcast

Josh’s BFFs Podcast, co-hosted with Dave Portnoy, became a central hub for discussing creator drama, business, and pop culture. It serves as his main media platform, allowing him to control his narrative and comment on past events, including his relationship with Nessa, from a position of authority.

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4. Nessa's Openness on Borderline Personality Disorder (BPD)

Nessa's decision to publicly discuss her diagnosis of Borderline Personality Disorder (BPD) on her IGTV series Life's A Ness was a powerful move. This transparency added depth to her public persona and resonated deeply with her fanbase, turning her into a mental health advocate.

5. The Co-Founding of Ani Energy

As part of his entrepreneurial journey, Josh co-founded the lifestyle energy drink Ani Energy. This practical business venture demonstrates his commitment to building tangible, consumer-facing brands beyond social media endorsements, further cementing his "business mogul" status.

6. The Enduring Legacy of the 'Jessa' Ship

Despite their definitive split, the "Jessa" relationship remains a high-interest entity. The continuous flow of questions and rumors, which Josh addresses on his podcast, ensures that both individuals remain relevant to the original fan base. The drama itself became a powerful, albeit painful, piece of content that propelled their careers forward.

7. The Strategic Use of Collaboration (Animal Capital)

Josh's business success is heavily dependent on his strategic partnerships. By forming Animal Capital with fellow creators like Noah Beck and Griffin Johnson, he utilized their collective influence and Gen Z insight to drive consumer awareness for their portfolio companies, a savvy fusion of fame and finance.

What is the Current Status of Nessa and Josh in 2025?

As of late 2025, Nessa Barrett and Josh Richards are fully committed to their separate, high-profile careers. Nessa is focused on her music and advocacy, consistently touring and releasing new material. Josh is immersed in the world of venture capital and media through Animal Capital and the BFFs Podcast.

While rumors about a potential reunion or lingering feelings occasionally surface—a testament to the enduring public interest in their story—Josh Richards has been clear: the "Jessa" chapter is over. Their story is a unique case study in the creator economy, demonstrating how a dramatic public breakup can be the catalyst for two distinct and powerful career transformations.