"They're like America's William and Kate, except in this case, both of them are attractive," the late-night host said.
Of assumptions that Ivanka would be a "moderating influence" on the President, Oliver asked, "Is Ivanka really the moderating influence that people claim? And what in Jared's background justifies such a gigantic White House portfolio?"
Oliver said that Ivanka's ability to be "vague" and "likable" has helped her public image in the White House, somehow softening the public perception of the First Daughter.
Oliver referenced Ivanka's April appearance on "CBS This Morning" when she said, "My father agrees with me on so many issues, and where he doesn't, he knows where I stand... I think most of the impact I have over time most people will not actually know about," she told King.
"That's convenient!" Oliver said. "So we should just give her credit when good stuff happens, and blame others when bad stuff happens? That's not a job description of a political adviser, that's a description of an Old Testament God. And that answer there enables you to project whatever you want onto her based on secondhand rumors and assumptions."
"You may still like Ivanka," he said. "She can be appealing, and that's frankly not by accident. She's been trained in the art of Trump branding to be as vague and likable as possible so that everyone can plausibly think that she shares their values -- whether or not that's actually true."
Referencing her 2009 book "The Trump Card: Playing to Win" in which Ivanka said: "Perception is more important than reality. If someone perceives something to be true, it is more important than if it is in fact true. This doesn't mean you should be duplicitous or deceitful, but don't go out of your way to correct a false assumption if it plays to your advantage."
"She's pretty much telling you to your face not to trust any assumption that you are making about her," Oliver said. "So it is possible that she is doing nothing to moderate her father. The truth is: we may all be thinking that Ivanka is doing a lot more than she actually is, although the same can emphatically not be said of her husband, Jared Kushner," who he called a "creepily silent 36-year-old heir to a real estate fortune."
Oliver warned against false hopes when it came to Ivanka and Kushner helping to "moderate" the President. "I don't know enough about them to eviscerate them, just as you don't know enough about them to justify putting any real hopes in them," Oliver said. "If they are the reason you are sleeping at night, you should probably still be awake."