If you were listening to the Howard Stern Show in the late 2000s, you remember the shockwaves. It wasn't just another bit. When Jim Florentine asked Robin Quivers out on the air, the vibe in the studio shifted. This wasn't a Wack Packer looking for a handout or a porn star looking for a plug. It was a real, gritty, somewhat awkward connection between the "Queen of All Media" and a comedian known for prank calling people as a character named Special Ed.
People were obsessed. They still are, honestly.
For years, Robin’s love life was a vault. She had "Mr. X," the mysterious long-term boyfriend whose face we never saw and whose real name, Tony, didn't slip out until after they'd called it quits in early 2007. So, when Jim Florentine—the guy from Crank Yankers and That Metal Show—stepped up to the plate just months later, it felt like the ultimate crossover episode.
The On-Air Gamble
In August 2007, Jim was a guest on the show. Howard, being Howard, started poking around. He knew Jim was single. He knew Robin was single. He basically played matchmaker in front of millions of people. Jim didn't blink. He asked her out right then and there.
Robin said yes.
The fans went nuts. There was even a nickname: "Quivertine." It sounds like a vitamin supplement or a rare mineral, but for about a year, it was the biggest gossip item in the Stern universe. But here’s the thing: Robin is fiercely private. She hated the "Howard 100 News" team snooping around her dates. She reportedly even considered not "prepping" (if you know, you know) for the date just to keep things from moving too fast.
Why It Actually Worked (For a While)
You’d think a world-traveling, high-society enthusiast like Robin wouldn't mesh with a heavy-metal-loving comic who makes fart jokes for a living. But they actually had a lot in common. Both were fiercely independent. Both worked in the same industry. Jim wasn't intimidated by her fame or her money.
They did real-world stuff. They went to Florida. They hit up spas. They went to dinner at Nobu. For a minute, it looked like Jim might be "the one" to finally get Robin to settle down. Howard kept digging for sex details, but Robin kept the walls up. She admitted she had "feelings" for him and called him a "deep thinker."
Jim, for his part, was surprisingly respectful. He wasn't running to the tabloids. He was just a guy dating a woman who happened to be the most famous co-host in radio history.
📖 Related: Kylie Jenner Plastic Surgery Before: Why the Timeline Still Matters
The Breakup: No Villains Here
By July 2008, it was over.
There was no screaming match. No cheating scandal. No dramatic walk-off. Robin announced it on the air, stating the breakup was amicable. Interestingly, she revealed that Jim was the one who initiated it. He was "genuine and honest" about it, which is pretty rare in the world of celebrity flings.
So, why did they split?
🔗 Read more: What Really Happened With the Nicki Minaj Leaked Sextape
- Schedules: Jim was a road comic. Fridays and Saturdays? He’s in a different city. Robin’s schedule was the exact opposite.
- The Lifestyle: Jim later admitted in interviews that the "comedy life" ruins relationships. You're out four or five nights a week. It’s hard to build a life with someone when you’re never in the same time zone.
- The Spotlight: Every move they made was dissected by Howard, Artie Lange, and Fred Norris. That puts a heavy weight on a new flame.
Where They Stand Now
It’s been over fifteen years since they called it quits. In the years following the split, Jim would occasionally drop by the show. The tension was gone, replaced by a weirdly sweet friendship. Robin even called him one of her "best friends" at one point.
They cleared the air at a dinner in November 2008, and while the "Quivertine" shippers wanted a reunion, it never happened. Jim moved on, eventually having a son and continuing his career in stand-up and podcasting. Robin has remained famously single, focusing on her health, her travels, and her seat next to Howard.
Real Talk on Why We Still Care
We care because it was a rare moment of vulnerability for Robin Quivers. She’s the person who calls everyone else out on their nonsense. Seeing her navigate a public romance was humanizing. It showed that even the most guarded people want a connection, even if it doesn't end in a "happily ever after" wedding special.
✨ Don't miss: Did Tom Jones Marry Priscilla Presley? The Truth Behind Those Decades of Dating Rumors
If you’re looking for the takeaway, it’s basically this: relationships don't have to end in a fireball to be over. Sometimes, two people just realize the "math" of their lives doesn't add up, and they walk away with their dignity intact.
Next Steps for the Fans:
If you want to hear the raw history, go back and find the August 16, 2007, episode of the Stern Show. It’s the "origin story" of the whole thing. Also, check out Jim Florentine’s podcast, Everybody Is Awful, if you want to see the brand of humor that won Robin over in the first place. You’ll quickly see why they clicked—and why it eventually ran its course.