Donald Trump Reportedly Told Then-Wife Ivana Trump to "Never Look a Day Over 28"

Who: Real estate tycoon and sitting President of the United States, Donald Trump, 73, and businesswoman, former model, and professional skier Ivana Trump (née Winklmayr), 70.

How They Met: The pair reportedly met at a party in 1976, at which point Ivana was taking a break from being “the number-one model in Montreal for eight years,” so says “The Donald” (a global nickname Ivana happened to have started). They wed the following year and welcomed their first son, Donald Trump Jr., almost exactly nine months later. They welcomed daughter Ivanka in 1981 and son Eric in 1984.

Why We Loved Them: Hmm … Did we?

When They Peaked: In terms of dysfunction, Ivana and Donald’s peak was perhaps when he joked that her salary as president of the Plaza Hotel was “$1 a year — and all the dresses she can buy.” Or it could be when he directed her to "Never look a day over 28." Or maybe it was when he, before a vast audience on The Oprah Winfrey Show, said that they get along well because, “ultimately Ivana does exactly as I tell her to do.” Ivana returned to The Oprah Winfrey Show following her divorce from Donald four years later with a new message: “I will not let men dominate me anymore.”

The Breakup: Over the Christmas season in Aspen in 1989, a public fight was reported as Ivana learned that Donald’s rumored mistress, Marla Maples, was staying at their same resort. “She couldn’t pronounce my name, but she was asking me if I was Moola or whatever . . . and she just asked if I was the one who had been loving her husband for years,” Maples told Vanity Fair of her confrontation with Ivana. By February, the Trumps had announced their intention to divorce.

Donald’s infidelity wasn’t exactly a secret. Though Maples has claimed that she and Donald were friends until after his split, Trump wasn’t exactly convincing when discussing his own faithfulness. When Playboy asked him whether he and Ivana were monogamous, he replied, “I don’t have to answer that. I never speak about my wife — which is one of the advantages of not being a politician. My marriage is and should be a personal thing,” adding, “I think any man enjoys flirtations, and if he said he didn’t, he’d be lying or he’d be a politician trying to get the extra four votes. I think everybody likes knowing he’s well responded to. Especially as you get into certain strata where there is an ego involved and a high level of success, it’s important. People really like the idea that other people respond well to them.”

The divorce grew ugly, with Ivana contesting her pre-nup and claiming in a deposition that Donald had, on one occasion in 1989, “raped” her. She later clarified that she hadn’t meant “rape” in a “literal or criminal sense.” When reports concerning her deposition resurfaced in 2015, Ivana released a statement reading,"The story is totally without merit. Donald and I are the best of friends and together have raised 3 children that we love and are very proud of."

Early in the Trump administration, Ivana released a memoir about her relationship and history with Donald titled Raising Trump. In an interview with ABC News, Ivana boldly referred to herself as “first lady” and boasted of her close relationship with the POTUS, claiming to have a “direct number” to the White House.

Where They Are Now: Donald wed Maples in 1993, two months after the birth of their daughter, Tiffany Trump. After finalizing his divorce from Maples in 1999, Donald began dating Melania Trump (née Knauss), whom he wed in 2005. Donald and Melania welcomed son Barron the following year. Trump took office in January 2016.

Ivana, too, married twice after splitting from Donald. She wed Riccardo Mazzucchelli in 1995 — they split in 1997. In 2008 she entertained a brief marriage with actor Rossano Rubicondi, though they soon reconciled following their 2009 breakup. Ivana declared herself a “single woman” in June of 2019, but has since been spotted with Rubicondi.