People still talk about it. It’s been years since the Howard Stern Show airwaves were dominated by the "Quivertine" saga, but for long-term listeners, the short-lived romance between Robin Quivers and Jim Florentine remains one of the most fascinating blips in the show's history. It wasn't just a celebrity hookup. It was a collision of two very different worlds: the intensely private, high-society life of Robin and the gritty, heavy-metal, prank-calling world of Florentine.
Honestly, nobody saw it coming. Robin had just come off a massive, decade-long relationship with the mysterious "Mr. X." She was single, she was vocal about it, and then Jim Florentine—the guy known for Crank Yankers and a certain brand of "low-brow" humor—decided to shoot his shot.
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The On-Air Proposition That Started Everything
It happened in August 2007. Jim was a guest on the show, and the conversation turned to his dating life. He had recently gone through a tragedy—his long-term girlfriend, Jade, had committed suicide in late 2006. He was in a vulnerable place, but he was also Jim. When Howard pointed out that Robin was single, Jim didn't hesitate. He asked her out right then and there.
The studio went silent for a second. Robin, usually the one to shut down any personal advances with a sharp laugh or a deflective comment, actually said yes.
By August 16, 2007, Robin was admitting to the crew that she’d had a "little crush" on Jim for a while. It felt weirdly genuine. Howard was giddy, acting like a matchmaker who couldn't believe his luck. But Robin was already getting defensive. She knew the Howard 100 News team would be sniffing around for every detail, and she hated that.
Dating Under the Microscope
They didn't waste much time. Their second date involved drinks and a kiss at the door of her hotel room. Of course, Howard grilled her about it the next morning. Did he touch her? Was there tongue? Robin played it cool, claiming it was just a nice evening, but the chemistry was clearly there.
By September, they were "officially" dating.
It wasn't all smooth sailing, though. You had Artie Lange cracking jokes, the news team trying to track their every move, and fans calling in with "advice." They even got a couple name: Quivertine. Jim later admitted in interviews that the name was "the gayest thing" he’d ever heard.
They tried to have a normal relationship, which is hard when you're on the biggest radio show in the world. They went to Florida together. Jim paid for everything, which Robin found impressive. She called him a "deep thinker" and "amazing." For a minute there, it looked like the legendary bachelorette of the Stern Show had finally found her match.
Why the Quivertine Romance Fizzled Out
It lasted about a year. On July 28, 2008, Robin dropped the news on air: it was over.
She was surprisingly classy about it. There was no screaming match, no "he cheated" rumors, and no drama. She said Jim was "genuine and honest" and that he was the one who pulled the plug.
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So, what happened?
- The Schedule: Jim was a touring comic. Robin was up at 4:00 AM for the show. He was working clubs until 2:00 AM.
- The Lifestyle: Jim later explained that the comedy business ruins relationships. You're out five nights a week. You're traveling. You can't just go to dinner on a Tuesday night like a normal couple.
- The Privacy Gap: Robin is aggressively private. Jim is a guy who tells stories about "Crackfinger" (his friend with a gross habit) on national radio.
Jim eventually admitted that while they "hit it off," the pressure of the show and their mismatched lives made it impossible. He said they started to feel like they were forcing each other to go to places they didn't want to be. That's a recipe for resentment.
Where They Stand Today
Surprisingly, they stayed friends. Most "Stern Show romances" end in a bonfire of bridges, but this one didn't. In 2009, Jim came back on the show and they were perfectly comfortable together. Robin even called him one of her "best friends" at the time.
She joked that she didn't even remember the sex, which Jim took as a blow to his ego, but it was all in good fun. They had moved on.
For the fans, the Robin Quivers Jim Florentine era was a rare glimpse into the "human" side of Robin. We saw her go from being the untouchable queen of the news desk to a woman who was nervous about a second date.
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What you should take away from the Quivertine saga:
- Relationships are hard in the public eye. If you're dating someone with a radically different lifestyle, you have to find a middle ground early or it won't last.
- Amicable breakups are possible. Even in the toxic world of shock-jock radio, these two proved you can end things without burning the house down.
- Watch the old clips. If you want to see a different side of Robin, go back and listen to the August 2007 episodes. It’s a masterclass in how to handle an on-air proposition with grace.
If you’re interested in how high-profile figures navigate dating, you might want to look into how other Stern Show regulars like Howard himself transitioned from a very public divorce to a long-term marriage with Beth Stern. It's a similar study in balancing a massive public persona with a private heart.