Ivanka Trump's Biggest Childhood Wish Went Unfulfilled (& Donald Is Partially To Blame)

Ivanka Trump's relationship with her father, Donald Trump, has been full of ups and downs. Once upon a time, Donald's eldest daughter was his biggest supporter, defender, and possible successor to his business empire. However, Ivanka started distancing herself from her dad when he left the White House in 2020. In addition to becoming less vocal about her support for her father, she grew more comfortable with having honest discussions about her childhood. 

During a January 2025 appearance on the "The Skinny Confidential Him & Her Podcast," she recalled how she would head to the New York Plaza Hotel after school to watch everything her mother, Ivana Trump, got up to as CEO of the establishment. Of course, she also enjoyed the same experience with her father. Although Ivanka was grateful she got to spend time with her parents, she still admitted that one major wish from the experience went unfulfilled. 

"There was never explicit instruction," Ivanka asserted. "I kind of wish I'd gotten a little bit of that, sort of sitting me down and saying, "This is how I like to be, this is how I conduct myself, did you notice this?"' To get a better understanding of Ivanka's childhood needs that went unnoticed by her parents, we tapped into the expertise of Dr. Kim Van Dusen, LMFT, RPT (licensed child therapist, parenting expert). The expert professed that every child should ideally have their autonomy balanced with structure to enable them to feel secure. In the absence of such boundaries, children like Ivanka may be left to deal with several complex emotions.

During Dr. Kim Van Dusen's exclusive chat with The List, she detailed some of the ill effects that children like Ivanka Trump may face after growing up in an environment that lacks structure. "[The] lack of control may lead to anxiety, indecisiveness, a lack of confidence, and a need to seek control, which may lead to power struggles and disruptive behaviors," the child therapist explained. 

Still, Dr. Dusen professed that Donald and Ivana Trump's lead-by-example approach to parenting was a good idea overall because enabled them to positively use their influence over their kids to model good behavior. However, she admitted that the method was a double-edged sword, cautioning, "If a child is exposed to toxic role modeling, that child may end up resentful and rebellious, or following the same path as their parent, and it is difficult to break that generational cycle." 

However, Dr. Dusen was quick to note that the parenting approach had likely benefited Ivanka. It's worth noting that in Donald's eldest daughter's 2016 chat with CNN, she shared that he never pressured her to follow in his footsteps. Instead, Donald tried his best to talk her out of going into the real estate business because he wanted to ensure it was a passion of hers and not something she was doing out of external pressures. However, even with the parenting approach aside, there are several red flags in Donald and Ivanka's relationship that only get harder to ignore.