Donald Trump’s Shocking Dating History

The Donald is the man—the ladies man that is. He loves women and clearly as these photos attest, women love him. Most of his former flames are models and actresses, which isn’t that surprising because Trump has made it pretty clear that he cares a lot about how a woman looks. Take a peek at the president’s past love life!


Donald’s first wife was Ivana. She was his wife for more than 15 years and is the mother of three of his children--Donald Jr., Eric and of course Ivanka, who looks remarkably like her mom. Rumors began circulating about Donald’s affair with Marla Maples, and Ivana filed for divorce. She and Marla even had a very public catfight over Donald. But the two remain friends, and enjoy sharing their 8 grandchildren.

Marla Maples

Donald eventually wed Georgia beauty queen Marla Maples after dating her for a couple of years following his divorce from Ivana. In fact, Marla was pregnant with Donald’s daughter Tiffany while they were still dating, and they tied the knot just two months after her birth. The marriage did not last long (1993-1999) and ended in divorce once again for Trump. Maples very famously and publicly declared that Trump was the best sex she ever had, and in 2013 told People Magazine that she still loved him

Anna Nicole Smith

Even though he was supposed to be with Marla after the breakup with Ivana, Donald was rumored to be sleeping with model Anna Nicole Smith, though neither of them ever kissed and told. They were spotted in public together on a fairly frequent basis.

Allison Giannini

Allison Giannini was only 27 years old when she met Donald on a blind date set up by a mutual friend. She couldn’t believe that her date was the 50-year-old and newly single billionaire. They went on a couple of dates but never had a serious relationship.

Rowanne Brewer

Rowanne Brewer was Donald’s next bad romance, as Lady Gaga would say. Another model, Brewer dated Donald for a long while but they never were married. Brewer really wanted to be an actress and she moved to L.A., leaving The Donald behind in New York. She defended Trump during the 2016 election, saying that he treated women very well.

Kara Young

Kara and Donald dated in 2001, but Kara was also dating another guy named A.J. Benza. When Benza told Howard Stern he was dating Kara, Donald Trump got a little territorial and called in to Howard’s show to say that he was also dating Kara. Yikes—that’s a tense love triangle.

Carla Bruni

Italian bombshell Bruni has a long list of ex-lovers, including Mick Jagger. Donald claims that Bruni was still in love with Jagger, so their dating life didn’t work out. Trump has only the nicest things to say about Bruni, who is currently married to the former French president, Nikolas Sarkozy.

Victoria Zdrok

Former Playboy model Victoria went on several dates with Donald, but said he was a real turnoff because he only talked about himself and his prowess in the bedroom.


By now, of course everyone knows that the stunning Slovenian-born model Melania is Trump’s third wife. Although they met at a party in 1998, they married years later in 2005. The long wait was mainly due to the prolonged divorce from Marla Maples. Let’s call it like it is—Melania is a stone cold hottie. Their amazing wedding was attended by many celebrities, including none other than---wait for it--- Bill and Hillary Clinton. Personal friend Billy Joel provided the entertainment—must be nice!.In 2006, Melania gave birth to their son Barron. Donald claims they are uber compatible and have never had a fight.

Jackie Siegel

Although they were never seen together, years later, Jackie said that she had gone on a couple of dates with Trump. Things never got serious, but Siegel, a former beauty pageant director, only had praise for Trump. “He’s really a great person. So much charisma. I’m so glad we’re still friends,” she told the Huffington Post.

Peggy Fleming

Three-time Olympic champion figure skater Peggy Fleming says that rumors of her romantic association with Trump are“untrue, unfounded and outrageous”. Back in 1990, the New York Daily News named Fleming as one of Trump’s possible mistresses, yet at the time, Fleming was married with two children

Catherine Oxenberg

Glamorous actress Catherine Oxenberg was a star of the long running TV series Dynasty and has also played the role of Princess Diana in two different TV movies. In the early 1990’s, she was rumored to be having an affair with Trump. Oxenberg called the rumors “a complete joke as far as I’m concerned. I hardly know the man,” she said.

Georgette Mosbacher

The cosmetics baron would just say “I don’t know what you’re talking about,” when asked about her alleged love liaisons with Trump. Mosbacher and Trump are the same age and have known each other for three decades. She describes Trump as "a gentleman”, "authentic," and "charming." But she was surprised when he tossed his hat in the ring for the presidential bid. “As long as I’ve known Donald, it never occurred to me [that he would run for office]!” Mosbacher attended his wedding to Melania and says "this idea that he hates women is just..." She shook her head. "To have known him as long as I've known him, that's the antithesis of him."

Carol Alt

The drop dead gorgeous supermodel and Sports Illustrated Swimsuit Issuecovergirl model was rumored to have dated Donald. She was insulted by this gossip because at the time she was married to Ron Greschner of the New York Rangers.

Next Post