USJUL 22, 2025
Trump’s Cringe Dating Remark On Howard Stern Returns To Bite Him
A 2006 interview of U.S. President Donald Trump on Howard Stern has resurfaced, sparking fresh backlash as public interest in Trump’s past relationship with Jeffrey Epstein intensifies.
Donald Trump appeared numerous times on The Howard Stern Show in the late 1990s and early 2000s.
In one such interview, Stern pressed Trump about his dating preferences.
Highlights
- A 2006 Howard Stern interview of Trump resurfaced amid rising scrutiny over his relationship with Jeffrey Epstein.
- Trump claimed he could date 24-year-olds at age 60 and awkwardly addressed his lower age limit for women.
- Past interviews revealed Trump’s controversial comments about his daughter Ivanka and young women.
Clips of Trump from the late 1990s and early 2000s have resurfaced amid the Epstein drama
Image Credits: Getty Images
“Do you think you could now be banging 24-year-olds?” Stern asked. Trump, then 60 years old, responded, “Oh, absolutely! I have no trouble.”
The conversation took an uncomfortable turn when co-host Robin Quivers asked Trump about his age limit for women, while he meant it as Trump’s upper limit, Trump fumbled at the response.
He then got his bearings, responding, “I don’t want to be like Congressman Foley, with, you know, 12-year-olds,” he said, referring to former Congressman Mark Foley, who had then recently resigned over sexually explicit messages to underage congressional pages.
“If I… No, no, I have no age... I mean, I have an age li…”
The comment, intended as a joke, has drawn criticism online.
The attention on Trump reached a new high last week following a Wall Street Journal report detailing a suggestive birthday message Trump allegedly wrote to Epstein in 2003.
The note featured a cryptic dialogue between “Donald” and “Jeffrey” exchanging vague references to “secrets” and “enigmas” that “never age.”
It also included a drawing of a woman’s breasts, allegedly by Trump.
Trump denied writing the message and has since sued the paper.
Last week, The New York Times also reported that Trump once hosted a calendar girl contest at Mar-a-Lago in 1993—with Epstein as the sole guest.
Image credits: Davidoff Studios/Getty Images
These reports have only intensified scrutiny of their friendship.
Trump has tried to downplay the Epstein scandal, dismissing it as a Democratic “hoax.”
But as Epstein-related stories continue to emerge, so do damaging reminders of Trump’s past behavior.
His old appearances on Stern’s show are now being mined for more controversial content, particularly moments when he discussed young women.
During a 2004 appearance on the show, Trump agreed when Stern referred to his daughter Ivanka as “a piece of a**.”
In 2004, Trump agreed with radio host Stern, referring to Trump's daughter as "a piece of a**"
Image credits: Benjamin Lowy/Getty Images
Trump also told Stern in 1999 that he had promised Ivanka when she was 17 that he’d never date a girl younger than her.
“So as she grows older, the field is getting very limited,” he said.
In another video from 1992, released by Entertainment Tonight in 2016, Trump can be heard asking, “Thursday night, you’re going up the escalator?” A child’s voice could be heard saying, “Yes.”
Trump then responded with “I’m gonna be dating her in 10 years. Can you believe it?”
The resurfacing of the clip comes just days after the Department of Justice and the FBI declared there was no evidence of foul play in Epstein’s prison death.
Officials also denied the existence of a hidden “client list,” frustrating MAGA supporters, especially since the Trump administration, at various points, acknowledged the existence of the Epstein files.
Trump had previously played into speculation about the Epstein investigation, but in recent weeks has dismissed it.
Critics argue these resurfaced stories, along with Trump’s old interviews, cast doubt on his claims of having had only a casual friendship with Epstein.
Image credits: Anna Moneymaker/Getty Images
In 2002, Trump famously told New York Magazine that Epstein “likes beautiful women as much as I do, and many of them are on the younger side.”
Trump has since tried to distance himself from Epstein, especially after the financier was arrested and later found dead in a Manhattan jail cell in 2019.