Inside Donald Trump's Relationship With Tiffany Trump

Let's be honest: For just about forever, 99 percent of the world had no idea that Donald Trump had a daughter other than his almost-far-too-beloved Ivanka. Indeed, Tiffany Trump – The Donald's daughter with ex-wife Marla Maples – flew largely under the radar for most of her life until The Apprentice host became a serious candidate for the presidency in 2016.

Born on Oct. 13, 1993, in West Palm Beach, Fla., Tiffany was raised in Calabasas, Calif. by Maples, completely across the country from her famous father. While speaking with People in 2016 about this dad-daughter relationship, Tiffany said, "We see each other as much as possible and of course we speak on the phone. I think regardless of distance, I don't think that dictates any relationship strains. I really have an emotional bond with him and he was always just the funniest, most loving father. I'm so lucky to have parents who are so supportive of me, of each other."

Of course, there is a lot of debate as to just how supportive Donald Trump is of daughter Tiffany ... which many insiders allege may be less than she says.

President Donald Trump's personal assistant, Madeleine Westerhout, was fired in late August 2019 after she revealed details about his family to the press, CNN reports — and one of those details was about POTUS allegedly body-shaming daughter Tiffany Trump over her weight. According to Politico, Westerhout claimed that Donald loved her more than his own daughters and alleged that Tiffany should lose weight before she's photographed with him. Westerhout was also accused of saying the president wouldn't be able to pick Tiffany out of a lineup.

While most parents would be mortified and furious with an employee who insulted their children, the president didn't sound too angry with Westerhout, despite her subsequent dismissal. "While Madeleine Westerhout has a fully enforceable confidentiality agreement, she is a very good person and I don't think there would ever be reason to use it," Trump tweeted. "She called me yesterday to apologize, had a bad night. I fully understand and forgave her! I love Tiffany, doing great!"

Swerve! Tiffany Trump reportedly dodged a kiss from her father at an October 2016 presidential debate. Us Weekly reports that the awkward moment went down at the conclusion of his Oct. 9, 2016 showdown with Democratic candidate Hillary Clinton. 

When each candidate welcomed their families onstage, Donald Trump appeared to lean in to kiss Tiffany on the cheek. However, he missed, because when he attempted to do so, she turned her head to look behind her and speak to someone else. A clip of the moment shows Tiffany leaning back away from her dad as he approaches her, but then rubbing his arm in an apparent effort to look a bit warmer towards him. 

While it's obviously not totally certain whether Tiffany dodged her dad's display of affection deliberately (say that five times fast), she did it so smoothly that one has to wonder if it wasn't the first time that it's happened.

According to a source cited by People in April 2018, becoming President of the United States has reportedly caused a further chasm between Donald Trump and daughter Tiffany. "Since the inauguration, Tiffany and her father have sometimes gone for months without speaking and she went a very long time without seeing him," the insider claimed. "The last time she was at a family function with him, it was awkward for her and she didn't feel totally welcome." The source said that they had a few moments in which they bonded during The Donald's presidential campaign, but noted that once he took office, things supposedly went by the wayside: "They always had a strained relationship [for] her whole life, and it got exacerbated by the presidency. It's gotten much worse now."

Still, a separate insider claimed that while Tiffany and Donald Trump don't have an "easy" relationship, they don't necessarily have a bad one. For example, this second source alleged that Tiffany spends holidays at the White House with her father.

If you ask Marla Maples, "dad" may as well be an honorary title for Donald Trump in regards to his relationship with daughter Tiffany — though Maples acknowledged that The Donald funded their lifestyle well. Maples and Tiffany lived in Calabasas, Calif. following Maples' 1999 divorce from the future president, far from his Big Apple headquarters. "Her daddy is a good provider with education and such, but as far as time, it was just me," Maples told People in 2016. "Her father wasn't able to be there with day-to-day skills as a parent. He loves his kids. There's no doubt. But everything was a bit of a negotiation."

She added, "I would bring her into New York a couple times a year and let her go see her dad in the office and let her go have dinner with him and Melania." Maples, who frequently reiterated that Tiffany was raised by a single mom, also said she wanted to ensure Tiffany had a healthy relationship with her father on a consistent basis.

Whoops! Donald Trump may have accidentally revealed that daughter Tiffany was an "oops baby." In 15 hours' worth of audio from The Howard Stern Show released to Newsweek, The Apprentice alum reportedly recalled getting the news of Marla Maples' pregnancy with little enthusiasm. "I'm glad it happened. I have a great little daughter, Tiffany," Trump said during an interview with the shock jock in 2004. "But, you know, at the time it was like, 'Excuse me, what happened?' And then I said, 'Well, what are we going to do about this?' [Marla] said, 'Are you serious? It's the most beautiful day of our lives.' I said, 'Oh, great.'" 

Donald reportedly also revealed that he thought Maples was on birth control when they conceived Tiffany. In another Stern segment (also via Newsweek), he discussed how each time he had another kid, the inheritance for each one shrunk proportionally, quipping, "Well, you know, it does cut up the pie as you keep producing."

When a then-15-year-old Tiffany Trump wanted an increase in her funding from her wealthy father, her beloved big sister helped out. Ivanka Trump claimed in her book, The Trump Card: Playing to Win in Work and Life, that she convinced Donald Trump to give Tiffany her first credit card for Christmas "with a small monthly allowance on it." Ivanka wrote, "If she'd been living in the same house with our father, she'd have been able to go up to him from time to time and ask for a little something extra. And he would have been inclined to give it to her." She added, "There were even times when he would just surprise [me and my brothers] with with a nice gift for no reason at all, on no special occasion, and I imagine Tiffany didn't get to enjoy the same surprises, just by virtue of lack of proximity."

A source told Vanity Fair that Tiffany was reportedly granted exactly $500 a month from her father while she was a student at the University of Pennsylvania, and that she was frugal and followed her budget to the cent. Meanwhile, the New York Post reported that Tiffany couldn't get a designer dress for the 2016 Republican National Convention, but was allegedly too embarrassed to borrow one from Ivanka, telling photographer Scott Nathan, "I don't want her to know I don't have any money."

Donald Trump has famously made comments about the attractiveness of his eldest daughter, Ivanka. While he hasn't publicly creeped anyone out regarding Tiffany lately, he did reportedly make comments about her when she was first born that would rub many the wrong way today. When Tiffany was an infant, Trump apparently told Entertainment Tonight that she had his lips, but hoped she would "grow out of that" (via Vanity Fair). While that seems innocuous enough, it was in another interview in 1994 on Robin Leach's Lifestyles of the Rich and Famous that Trump got weird. Of his then-baby girl, he told the host, "She's got Marla's legs. We don't know whether or not she's got this part yet." Trump gestured to his chest, then added, "But time will tell."

In 2016, Leach defended Trump's language to Inside Edition (via the New York Daily News), griping, "I think it's an overreaction to be really honest, and I think that it's just the piling on of those that dislike Donald. You've triggered a thought that I should send him a note saying, 'Sorry I asked the question 22 years ago. How ridiculous they dig it up now.'"

Tiffany and Donald Trump might not be very close in part because they didn't actually live physically close to one another for a long time. "There are some who will tell you that Tiffany is not as much in the mix as his other children because he didn't have a good relationship at the end with Marla," a source told People in 2018, adding that this physical distance played a role in the supposed emotional distance between the father and daughter. "So Tiffany didn't get to be as intimately involved with the family dynamic as Ivanka, Eric and Donnie Jr. She doesn't really talk about her dad a lot. She's always been somewhat independent of the whole family."

The president himself may have inadvertently dissed Tiffany during a 2016 call to Fox News, in which he boasted of his offspring, "I'm very proud of my children" (via Mashable). Trump added, "I mean, I'm just looking at them right now as an example ... but I'm very proud 'cause Don and Eric and Ivanka and, you know, to a lesser extent 'cause she just got out of school, out of college, but, uh, Tiffany, who's also been so terrific. I mean, they work so hard." 

Of course, Donald likely didn't mean any harm and just had a clumsy choice of words, but ... ouch.