It started with a podcast interview and ended with some very explicit text messages that had everyone on the internet doing a double-take.
Honestly? If you’ve been following the chaotic Venn diagram of reality TV royalty, you know that Harry Jowsey and Kristin Cavallari are two names you wouldn't necessarily put together on a bingo card. She’s the refined, "I-have-it-all-together" mogul from Laguna Beach. He’s the self-proclaimed Australian "player" who basically became the face of Netflix’s Too Hot to Handle.
But in early 2025, things got weird. And then they got loud.
The Morning Wood Text That Changed Everything
The whole saga blew up during Kristin’s Honestly Cavallari: The Headline Tour. While sitting on stage in front of a live audience, Kristin didn’t just hint at a flirtation—she pulled out the receipts.
Apparently, she woke up one morning to a very specific kind of notification. A "d--k pic" from Harry Jowsey.
"It was 7 a.m.!" she joked to the crowd. "Like, morning wood."
Harry, who was actually a guest on her tour at the time, looked like he wanted to dissolve into the floorboards. He was literally thumping his microphone against his forehead in embarrassment. But he didn’t deny it. In fact, he later went on his own podcast, Boyfriend Material, to clear the air about it.
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He called it a "Hail Mary."
Basically, he wanted to see if there was a "nibble."
The wildest part isn't even the photo itself. It’s that Kristin, in her typical unfiltered fashion, decided to fire back. The next day, she sent him a lingerie photo because, as she put it, she "woke up horny."
That is some high-level chaos.
Are They Actually Dating?
Despite the NSFW digital exchange, the answer is... probably not. Or at least, not seriously.
Kristin has been very open about the fact that she knows exactly who Harry is. She’s called him an "absolute player" and even admitted she’s already "done the young thing," referring to her seven-month relationship with 24-year-old TikToker Mark Estes that ended in late 2024.
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The chemistry between her and Harry is undeniable. You can hear it in their podcast episodes—they giggle, they flirt, they tease each other about "sexual tension." But Kristin told Us Weekly that while she thinks he has a "big heart" and is "the sweetest," there isn't necessarily a long-term romantic spark there for her.
Harry's Moving Target
If you’re trying to keep track of Harry’s love life in 2026, you’re going to need a spreadsheet. Just as the rumors about him and Kristin were peaking, he was spotted:
- Dating actress Lucy Hale (though that reportedly fizzled out because, well, Harry is Harry).
- Holding hands with singer Sia in July 2025.
- Most recently, getting extremely cozy with OnlyFans star Anna Paul.
By the end of 2025, Harry and Anna Paul were all over TikTok, going to Coldplay concerts and posting videos with captions like "what’s the point in having ChatGPT when you can have a girlfriend who’s always right."
So, while the "d--k pic" heard 'round the world made for great podcast content, it seems Harry moved on to the next headline pretty quickly.
Why We Care So Much
There's something fascinating about watching Kristin Cavallari navigate her 30s. She’s a mom of three, a massive business owner, and yet she’s fully embracing this "flirty era" where she doesn't give a damn about what the tabloids say.
She told her audience she wants to "give them something to write about."
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Mission accomplished.
She’s also been linked to a mystery "big deal" sports coach recently, arranged by her agents at CAA. She hasn't named him yet, but she did say she wasn't really feeling the sparks after the first date. It seems she’s looking for depth—something she’s not sure Harry Jowsey is ready to provide quite yet.
What Most People Get Wrong
The biggest misconception is that this was a "scandal." In reality, it was two single, attractive people being messy on purpose for entertainment.
Harry was actually in a period of celibacy for a while following the death of his father in late 2024. He told Kristin that he "wasn't horny" and was trying to evaluate himself as a future husband and dad. The "Hail Mary" text to Kristin might have been his way of testing the waters as he got back into the game.
Key Takeaways from the Jowsey-Cavallari Flirtation:
- The NSFW Exchange Was Real: Both parties confirmed they swapped explicit photos, but Harry claims his was "selective" and more of a "boxer shot" than a full-on reveal.
- It Was Never Serious: Kristin respects Harry but views him more as a "sweet guy" with a bad reputation than a potential partner.
- Kristin is Controling the Narrative: She uses her podcast to air her own "scandals" before the paparazzi can spin them.
- Harry is Busy: With his new Netflix dating show Let’s Marry Harry premiering in 2026, he’s leaning into his brand as the guy everyone wants to fix.
If you’re looking for a lesson here, it’s probably that "selective" texting is a dangerous game when you’re dealing with a woman who has a live microphone and a podcast tour.
To stay updated on Kristin’s revolving door of mystery dates or Harry’s latest TikTok launch, the best move is to keep an eye on their respective Instagram stories—they usually tell on themselves long before the news outlets catch up.