Kat Stickler and John Mayer: What Really Happened Behind Those New York City Dates

Kat Stickler and John Mayer: What Really Happened Behind Those New York City Dates

You know how the internet collectively loses its mind whenever two people from completely different universes are spotted at the same table? Yeah. That’s exactly what happened when the world saw TikTok powerhouse Kat Stickler and guitar god John Mayer sitting together in New York.

It was October 2025. People were just minding their own business, scrolling through DeuxMoi, and then—bam—there they are. Tucked into a booth at a members-only club. Very touchy. Very cozy. It felt like a glitch in the simulation.

Honestly, nobody saw this coming. Kat had just come off a whirlwind of a year, including a breakup with The Bachelorette alum Jason Tartick and a mysterious "soft launch" of another guy that seemed to vanish into thin air. Then Mayer, the man who basically wrote the manual on high-profile Hollywood dating, enters the chat.

The Timeline of the Kat Stickler and John Mayer Rumors

Let's look at the receipts. Because there are plenty of them.

The whole thing kicked off in earnest around October 10, 2025. They were spotted at a private club in NYC, followed immediately by another sighting the very next night at the Flyfish Club. Two nights. Back-to-back. In the world of celebrity dating, that’s usually code for "we’re definitely more than just friends grabbing a salad."

Insiders told Us Weekly that Mayer was the one who actually sought her out. He pursued her. Hard. He was texting her often, inviting her out, and doing the whole "active pursuit" thing.

👉 See also: Why Taylor Swift People Mag Covers Actually Define Her Career Eras

But here’s where it gets interesting: Kat wasn't necessarily looking for her next Great Love. Sources close to the 31-year-old creator said she thought it would just be "fun" to date again. She was reportedly in a headspace where she didn't think it would be serious. She just wanted to enjoy the vibe after a string of heavy transitions in her personal life.

Why Everyone Is Obsessed With This Pairing

It’s the contrast. Kat Stickler is the relatable, hilarious mom next door who built an empire on 60-second clips of her being chaotic and real. She has over 12 million followers who feel like they know her soul.

Then you have John Mayer.

He’s 48. He has a 17-year age gap with Kat. He has a dating history that reads like a Grammy nominations list—Taylor Swift, Katy Perry, Jennifer Aniston, Jessica Simpson. For a lot of Kat’s fans, this felt like a "cautionary tale" waiting to happen. There were literally comments on her TikTok saying, "Run, Kat, run!" and "Please tell us this isn't real."

But Mayer has been singing a different tune lately. He’s been vocal about his "reliability kink." On the Comfort Food podcast, he admitted he "absolutely" wants to get married and wants someone to rely on him. He's over the "Lothario" reputation. Or so he says.

✨ Don't miss: Does Emmanuel Macron Have Children? The Real Story of the French President’s Family Life

Is It Getting Serious in 2026?

By December 2025, the narrative shifted. What started as "just for fun" apparently took a turn. Reports started surfacing that they spent Thanksgiving weekend together. That’s a massive milestone. You don't usually do turkey and stuffing with someone you're just "casually" texting.

Word is she’s even met some of his friends. When you're in Mayer’s inner circle, that’s a gated community.

Despite the serious reports, Kat has been classic Kat on social media. She posted a TikTok in late 2025 talking about her new bob haircut, joking that cutting your hair is a "tell-tale sign of a relationship gone bad" and claiming she was single. Was she trolling? Maybe. Was she protecting her peace? More likely.

The Realities of Dating in the Public Eye

We have to acknowledge the complexity here. Kat isn't just a "girl dating a guy." She’s a mom to her daughter, MK. Her fans are protective of that. There was a lot of noise on Reddit and TikTok about the speed of her dating life, but honestly, we only see about 1% of what’s actually happening.

Mayer has spent decades being the villain in other people's songs. He’s smarter now about how he handles his business. He knows that if he's going to date someone as public as Kat, every dinner at Torrisi or the Flyfish Club is going to be a headline.

🔗 Read more: Judge Dana and Keith Cutler: What Most People Get Wrong About TV’s Favorite Legal Couple

What Most People Get Wrong About Them

People love to put celebrities in boxes. They see the age gap and the "bad boy" history and assume they know the ending. But by early 2026, the buzz suggests they might actually be a decent match because of their humor.

Both are famously funny. Kat’s whole career is built on comedic timing. Mayer is known for his dry, often self-deprecating wit. If you've ever watched a John Mayer Instagram Live, you know he’s basically a stand-up comedian who happens to be a virtuoso at guitar.

Actionable Insights for Fans and Observers

If you're following this saga, here are a few things to keep in mind:

  • Don't take TikTok "single" posts at face value. Creators often use "single" content to maintain their brand or deflect heat from a private relationship that is still forming.
  • Watch the background details. If you start seeing familiar interior design in the background of Kat’s stories—or if John starts showing up in Florida—that’s your real confirmation.
  • Respect the transition. Whether this becomes a "power ballad of heartbreak" or a legitimate long-term partnership, both are navigating very public lives while trying to find something real.

The current state of the Kat Stickler and John Mayer connection is a "serious" evolution from what started as a casual New York fling. While they haven't given us the "hard launch" on the main feed yet, the sightings and insider reports suggest this is the most settled Mayer has looked in years.

To stay updated, keep a close eye on Kat’s subtle "soft launch" cues on TikTok—she's a master of the hidden detail—and check John's touring schedule, as he often frequents the cities where his heart is currently located.