Summary
- Trump and Stern shared intimate and controversial conversations about dating life and relationships in the 1990s.
- Trump made inappropriate comments about his dating habits.
- Trump openly discussed his preference for dating young women.
Donald Trump and Howard Stern both have a reputation for saying what they want and sometimes offending others. It makes sense that in the 1990s, Stern interviewed the former President frequently. Although Stern made fun of Donald and his daughter Ivanka and the two haven't gotten along for a while now, they once had some memorable conversations. While it doesn't take much for Trump to open up, Stern seemed to have a unique way of getting the public figure to say some pretty outrageous things.
While Trump and Stern discussed various topics during their chats, they always circled back to Trump's thoughts about his love life. Given the misconduct allegations against Trump and the fact that he has been married three times, his dating life has always been filled with controversy. In this article, we'll take a look at the comments Donald Trump made about his dating life during a few Howard Stern interviews.
Donald Trump Made Disturbing Comments About STDs In A Howard Stern Interview
In the 1990s, Howard Stern interviewed Donald Trump several times and talked about being glad that he didn't contract any STDs. While many would say this was a personal and intimate subject that a public figure shouldn't discuss in an interview, he opened up quite a lot.
According to People, Trump said during a 1993 interview:
"You know, if you're young, and in this era, and if you have any guilt about not having gone to Vietnam, we have our own Vietnam — it's called the dating game. Dating is like being in Vietnam. You're the equivalent of a soldier going over to Vietnam."

Donald Trump Shamed Angelina Jolie For How Many Men She'd Been Intimate With During Her Marriage To Brad Pitt
During Angelina Jolie and Brad Pitt's marriage, Donald Trump criticized her and shamed her for how many people she'd been intimate with.
Trump said something similar back in 1997. He called a woman's private parts "potential landmines," which was definitely shocking. He then said:
"It's amazing, I can't even believe it. I've been so lucky in terms of that whole world, it is a dangerous world out there. It's like Vietnam, sort of. It is my personal Vietnam. I feel like a great and very brave solider."
Donald Trump was married to his second wife Marla Maples at the time of these Howard Stern interviews. If there is one thing that people can say about the political figure, it's that he doesn't mince words when it comes to his many marriages. Even though he was married, he was still honest about being an active part of the dating world.

Donald Trump May Have Still Cheated On His Wife If She Hadn't Accidentally Met His Mistress
Donald Trump once admitted that he may have continued cheating on Ivana Trump if she didn't catch him and Marla Maples.
Also in the 1990s, Donald Trump spoke to Joan Rivers about his intimate life, and they had a conversation similar to his talk with Howard Stern. When Rivers commented, "If you had slept with every woman they [the media] claimed you slept with…” Trump said, “I’d be dead. One way of the other, from whatever or from whatever.” This comment seems to suggest that he didn't date as much as the press claimed.
However, as The Mirror reported, Trump has a long dating history besides his three wives. When he said that he was proud to have avoided STDs, he seemed to be saying that he had slept with a lot of women. People can only speculate about exactly how many women Trump has been intimate with, though.
Donald Trump Talked To Howard Stern About Dating Young Women
In 2016, CNN reported that some of Howard Stern's Donald Trump interviews focused on Trump being interested in dating young women. These remarks are even more disturbing when people think about Trump's age during these interviews.
When Stern interviewed Trump in 2006, Trump was 60 years old. Stern inquired about the youngest woman that the politician would date. Trump said of having "an age limit" when it came to his dating life:
“No, I have no age — I mean, I have age limit. I don’t want to be like Congressman Foley, with, you know, 12-year-olds.”
When asked if he saw himself dating women who were 24 years old, Trump said, "Oh absolutely." He added, "I'd have no problem."

Donald Trump's Actual Family History Proves He Was Lying About His Ancestry For Years
For years Donald Trump spoke about his ties to Sweden, but the former President has a different family history.
Who Are Donald Trump's Three Wives?
- first wife: Ivana Trump (married 1977-1990)
- second wife: Marla Maples (married 1993-1999)
- third wife: Melania Trump (married 2005-present)
CNN also reported that back in 2002, Donald Trump spoke to Howard Stern about how women who were 30 were "a perfect age." When someone added that Trump didn't want to date someone who was 35 years old, Trump agreed. He then said something that many would find offensive:
“What is it at 35? It’s called check-out time."
At the time of this 2002 interview, Donald Trump was 56 years old. Trump has always been much older than the women he has dated seriously, and from his Howard Stern interviews, he made it clear that this is exactly how he wanted it.
Trump is 24 years older than his third and current wife Melania, who is 56. He was 17 years older than his second wife Marla Maples, who is 60 years old. However, Trump was only a few years older than his first wife, the late Ivana Trump.
Trump has dated many younger women. According to The Mirror, he dated Allison Giannini for a short period at the age of 50. Since she was 27, there was a huge age gap. Trump also dated Rowanne Brewer Lane in 1990 when she was 26 and he was 44.
What Were Some Of Howard Stern's Most Offensive Interviews? (According to Buzzfeed)
- asked Anna Nicole Smith to get on a scale
- talked about Mariah Carey's body
- said he would be intimate with Heather Locklear
- criticized Marilyn Manson's ex Rose McGowan when talking to Manson
However, even though he is known for marrying younger women, it's still pretty memorable to hear him say that he would date a 24-year-old when he was 60.
The entire time that Donald Trump has been a public figure, he has made disturbing comments. In 2016, Vox reported on a video of Trump from 1992. Trump said of a young girl, "I am going to be dating her in 10 years. Can you believe it?"
While Donald Trump's remarks are tough to hear, Howard Stern admitted on The Late Show with Stephen Colbert in 2016 that Trump was an entertaining person to interview because of his outspoken nature. According to CBS News, Stern said:
"But [he was] a great guest because he would say anything that came into his mind. He was completely unfiltered, he was talking about [how] his daughter was the most attractive woman he ever met and how much he thought she was hot."