If you were a Directioner in 2013, your Twitter feed was probably a war zone of grainy paparazzi shots and frantic speculation. It was a weirdly specific era. Harry Styles had just come off the massive, public whirlwind of "Haylor"—his brief but legendary relationship with Taylor Swift—and everyone was waiting to see who’d be next.
Then came Kimberly Stewart.
She wasn't a fellow pop star or a rising indie actress. She was a 33-year-old socialite, model, and daughter of rock royalty Rod Stewart. Harry was 19. The 14-year age gap sent the internet into an absolute tailspin. But was it just a fleeting hookup, or did Rod Stewart actually leak one of the industry's most private flings?
The Night at Dan Tana’s
It all started in West Hollywood. If you want to be seen in LA while pretending you don't want to be seen, you go to Dan Tana’s. In April 2013, Harry was spotted there with the ultimate "meet the parents" crew: Rod Stewart, his wife Penny Lancaster, and Kimberly.
People weren't just looking at the pasta. Sources at the time claimed Harry and Kimberly were "cuddly" and "holding hands" right in front of her dad. Now, Harry has always had a thing for older women—that’s not exactly a secret. But joining the Stewart family for dinner felt different. It felt like a "thing."
The next morning, the "proof" dropped. Harry was spotted grabbing coffee in LA, and eyewitnesses claimed Kimberly was waiting for him in the car.
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Rod Stewart: The Accidental Gossip King
The real confirmation didn't come from a rep or a glossy magazine spread. It came from Rod Stewart himself, who apparently didn't get the memo about PR discretion.
During an appearance on Alan Carr: Chatty Man shortly after the dinner, Rod was asked about the rumors. He basically fumbled the bag in the most hilarious way possible.
"His [Harry's] car was here in the morning. Let’s put it that way," Rod told the host.
He then immediately realized he’d messed up. He muttered something about how Harry might have just "come round to pick something up" before eventually giving up and saying, "Bollocks, I’ve let the cat out of the bag."
He didn't stop there. Rod went on to describe Harry as a "lovely fella" and even joked about Harry ruffling his hair the same way Rod does. It was the ultimate dad move—accidentally confirming your daughter’s fling on national television because you think the guy is a "good lad."
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Why the Kimberly Stewart Rumors Persist
Even though it was over a decade ago, this specific chapter of Harry's dating history stays relevant for a few reasons.
- The Rebound Factor: This was Harry's first real link after Taylor Swift.
- The Age Gap: A 14-year difference isn't huge in the real world, but in the 2013 boyband world? It was scandalous.
- The Family Tie: It wasn't just a random model; it was Rod Stewart’s daughter. It felt like a passing of the "British Rock Star" torch.
Honestly, it probably wasn't a long-term romance. Most insiders from that time describe it as a brief "fling" or a "hookup" rather than a serious relationship. By the time 2013 was winding down, Harry was already being linked to Kendall Jenner, and the Kimberly Stewart era was relegated to the "did that actually happen?" archives.
Was It Actually Ruby Stewart?
There’s always a conspiracy theory, right? Some fans at the time tried to argue that Harry was actually seeing Kimberly’s sister, Ruby Stewart. Ruby was closer to Harry’s age (25 at the time).
However, given Rod’s very specific comments about Harry’s car being at the house and the Dan Tana's sightings, the Kimberly connection has way more weight. Kimberly has always been a bit of a wild card in the socialite scene—she has a daughter with Benicio del Toro and a history of doing things her own way. A brief romance with the world's biggest boyband star fits her vibe perfectly.
What This Tells Us About Harry
If you look at Harry's history—from Caroline Flack to Kimberly Stewart to Olivia Wilde—there is a clear pattern of him being attracted to women who are established, independent, and often older. He’s never really played by the "teen idol" rules of dating someone his own age for the sake of the fans.
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The Kimberly Stewart situation was just the first time we saw how much he truly didn't care about the optics. He was happy to sit down with a rock legend, date his daughter, and deal with the fallout later.
Next Steps for the Curious
If you're trying to piece together the full Harry Styles lore, you should look into the timeline of his "One Direction: This Is Us" filming. Interestingly, the dinner with the Stewarts happened right around the time he was being interviewed for the documentary, where he famously said he hadn't "met a girl yet" who made the earth move for him.
Check out the archived footage of the Alan Carr: Chatty Man interview from May 2013 if you want to see Rod Stewart's legendary slip-up in real-time. It remains one of the most transparent celebrity "oops" moments in British TV history.