Donald Trump On A Then 18-Year-Old Lindsay Lohan: ‘Deeply Troubled Women’ Are ‘Always The Best In Bed’

By 10.14.16

Getty Images - Shutterstock

Turns out that all those appearances Donald Trump made on The Howard Stern show over the years are turning out to be not so great for his Presidential run.

On Thursday, we shared a clip from the show back in 2006 Trump jokingly admitted to being a “sexual predator.” Real funny stuff.

Now today, in audio unearthed by CNN, Trump was discussing a then 18-year-old Lindsay Lohan with Stern when he said even more things that seem rather unpresidential.

Here’s some of the conversation which took place the same year Mean Girls came out…

In an appearance on Stern’s show in December 2004, Trump initiated a conversation about actress Lindsay Lohan, who was 18 at the time.

“What do you think of Lindsay Lohan?” Trump asked Stern.

“I think she’s hot,” responded Stern.

“There’s something there right?” Trump said. “But you have to like freckles. I’ve seen a, you know, close up of her chest and a lot of freckles. Are you into freckles?”

“I’m not into freckles, but the red hair thing I like. I like her on the cover of Entertainment Weekly,” said Stern.

“Now does the father wreck, does that bother you a little bit?” Trump asked later in the conversation.

“Howard feels that the father being a wreck is a good thing,” interjected co-host Robin Quivers.

“Oh yeah, because first of all, if the father’s a wreck like the way he is–” Stern said.

“Right,” said Trump.

“Can you imagine the sex with this troubled teen?” said Stern.

“Yeah, you’re probably right,” Trump said. “She’s probably deeply troubled and therefore great in bed. How come the deeply troubled women, you know, deeply, deeply troubled, they’re always the best in bed?”

Stern responded, “Because they’re looking for love, they’re looking for positive affirmation, they’re looking for a father figure who will love them and tell them they’re wonderful and they’ll never be enough. No matter many times you tell them they’re beautiful, no matter how many times you tell them you love them they want to suck it up more. They would drain you like a vampire until your head caved in if they could get more love.”

“Well I have a friend Howard who’s actually like a great Playboy, I mean, I don’t say this about men, this guy does very well,” said Trump. “He runs silent, runs deep as they say, like a submarine. He will only look for a crazy women. He says, ‘Donald, Donald, please, please, I only want the crazy women.'”

“They’re desperate,” adds Stern.

“What is this guy all about,” said Trump. “But for some reason, what I said is true. It’s just unbelievable. You don’t want to be with them for long term, but for the short term there’s nothing like it.”

Eh, I’m sure that can all just be chalked up to “locker room talk,” right?

Listen the entire interview below…



Lindsay Lohan image: Featureflash Photo Agency /

Share This

TAGS2016 presidential electionDonald TrumpHoward Stern.Lindsay Lohan

Join The Discussion