"There's something there right?" Trump said before noting that Lohan has a lot of freckles.
"I've seen a, you know, close up of her chest and a lot of freckles. Are you into freckles?" Trump asked Stern.
Stern replied that he is not "into freckles" but that he likes Lohan's red hair.
Later in the discussion about Lohan, Trump asked Stern, "Now does the father wreck, does that bother you a little bit?"
Co-host Robin Quivers jumped in to say that Stern thinks "the father being a wreck is a good thing."
"Oh yeah," Stern said. "Because first of all, if the father's a wreck like the way he is ... you imagine the sex with this troubled teen?"
"Yeah, you're probably right," Trump said in response. "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 launched into his explanation for this supposed phenomenon, saying, "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."
Trump then brought up a friend of his who "is a great playboy" and "will only look for a crazy woman."
"What is this guy all about?" Trump asked. "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."