The world of TikTok royalty is messy. If you’ve been following the Sway House era or religiously listen to the BFFs podcast, you know that Josh Richards isn’t just a businessman with a knack for venture capital—he’s also been at the center of some of the most high-profile internet breakups of the decade. Honestly, trying to track the timeline of Josh Richards relationships is like trying to solve a Rubik's cube while riding a roller coaster.
It’s fast, it’s loud, and there’s always a new twist.
People love to speculate. Was it a PR stunt? Was there actual cheating? Most fans only see the 15-second clips or the cryptic Instagram captions. But when you strip away the filters, the reality of dating in the spotlight is a lot more complicated than a viral dance trend.
The Nessa Barrett Era: Love, Music, and a Whole Lot of Drama
We have to start with the big one. Josh and Nessa Barrett weren't just a couple; they were the couple. They went Instagram official in early 2020, and for a while, it felt like they were the king and queen of the TikTok scene. They were young, successful, and constantly posting PDA-packed content that had millions of "Zash" shippers obsessed.
Then came the June 2020 YouTube video.
In a video titled "We Broke Up," they sat on a bed and told the world they were calling it quits. It wasn't because of a huge fight—at least, that’s what they said then. They claimed they needed to grow up and focus on themselves. "We were in a very serious relationship, but we weren't ready for as serious as it was," Josh told PEOPLE at the time.
But the peace didn't last.
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The drama truly exploded when Nessa started working on music with Jaden Hossler, who happened to be Josh’s best friend. When Jaden and Nessa’s song "La Di Die" dropped, so did the bombshell: they were together. This sent the internet into a literal tailspin. Mads Lewis, Jaden’s ex, went on the warpath, and Josh was left in the middle of a messy love triangle that felt more like a octagon.
He handled it surprisingly well in public, mostly sticking to his "handling it offline" mantra, even though the betrayal of a best friend and an ex-girlfriend getting together is enough to make anyone want to delete their social media accounts forever.
The Gabi Moura Chapter: A New Kind of Stability?
Fast forward to late 2023. After a few years of being the "single bachelor" of the podcast world—and debunking rumors about everyone from Dixie D’Amelio to random college students—Josh finally went public with Gabi Moura.
Gabi is a Brazilian influencer with a massive following of her own (over 11 million on TikTok alone). Unlike the chaotic, drama-fueled days of his early 20s, this relationship felt... different. Kinda more grounded.
- How they met: Josh actually slid into her DMs back in 2021.
- The first date: He took her to Dave & Buster's. He calls it the "best place to get to know someone." Honestly? Respect for the arcade date.
- Living together: Because of visa issues, Gabi actually lived with Josh for a while when she first moved to Los Angeles.
They’ve been pretty open about their life together. They post dance videos, travel to Rio de Janeiro, and show up at New York Fashion Week looking like a power couple. In a January 2024 episode of the Bottoms Up with Fannita podcast, Josh confirmed they’d been dating since the summer of 2023.
As of early 2026, they are still going strong. While rumors of breakups occasionally pop up—usually because they haven't posted together for 48 hours—they’ve been quick to shut them down. It seems Josh has finally traded the high-stakes drama for something a bit more consistent.
The Rumor Mill: Mads Lewis and the Julie Jisa "Stunt"
You can't talk about Josh's dating history without mentioning the "what ifs" and the "maybes."
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There was a period where everyone thought he and Mads Lewis were dating. They were making flirty TikToks to shady songs, and the internet was convinced they were getting "revenge" on Jaden and Nessa. Josh eventually cleared the air on BFFs, admitting they had "hooked up in the past" but were ultimately just homies.
Then there was Julie Jisa.
In 2021, Josh posted a TikTok with Julie, a University of Florida grad, that looked very "relationship reveal." Fans went wild. But it turned out to be mostly for the cameras. He told Seventeen that they had only hung out twice and just wanted to film a funny video. It was a classic example of how easily a single 15-second clip can manipulate the entire internet’s perception of someone’s love life.
Why We Are Still Obsessed With Josh’s Dating Life
It’s not just about the gossip. Josh represents a specific generation of creators who grew up in front of us. We saw him go from a teenager in a house in Bel Air to a serious entrepreneur. Watching his relationships evolve from the "messy teenage drama" phase to "living with a partner" feels like watching a friend grow up.
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Also, he’s one of the few influencers who actually talks about the mechanics of dating in the industry. On the BFFs pod, he’s often the one dissecting other people's breakups, which makes his own romantic life even more of a focal point.
Moving Forward: What to Watch For
If you’re trying to keep up with Josh Richards relationships, don’t just look at the TikTok feed. Look at the guest list for the big events. Gabi Moura seems to be a permanent fixture in his life now, transitioning from a "rumored girlfriend" to a legitimate partner.
The main takeaway? Don't believe every "shady" TikTok sound you hear. In the influencer world, a song choice is often just a song choice, but a trip to Brazil to meet the parents? That’s the real deal.
For anyone following along, the best way to stay updated isn't through the comment section—it's through the BFFs podcast episodes where Dave Portnoy inevitably grills him about his personal life. Keep an eye on Gabi’s vlogs too; she often captures the more "human" side of Josh that doesn't make it into his business-focused content.
The era of the "Sway Boy" heartbreaker is over. The era of the settled-down mogul has officially begun.