If there’s one thing Donald Trump has never been shy about, it’s talking himself up. Long before the White House, before the campaign rallies and courtroom drama, there was the brash New York real estate developer who proudly embraced what he once called “truthful hyperbole” in The Art of the Deal, describing it as “an innocent form of exaggeration, and a very effective form of promotion.” That mindset didn’t just apply to skyscrapers and branding. It spilled into his love life, too.
Trump’s reputation as a ladies’ man goes back decades. In fact, he was reportedly crowned “Ladies Man” in his 1964 yearbook, and former classmates have suggested that title wasn’t just for show. One ex-classmate even told NPR that when it came to girls, “it was a revolving door.” That revolving door would later turn into tabloid headlines, whispered rumors, and very public scandals that followed him from Manhattan penthouses to Pennsylvania Avenue.
Early Dating Stories That Built Trump’s Reputation
Let’s start at the beginning, or at least, near it. Actress Candice Bergen once revealed she went on a dinner date with Trump when she was 18. She described him arriving in a burgundy three-piece suit, burgundy patent leather boots, and a burgundy limousine. Color coordination? Absolutely. Chemistry? Not so much. Bergen later said there was “no chemistry” and “no physical contact whatsoever,” later calling him, bluntly, “a good-looking guy” and “a d–che.” Ouch.
Another early date, Lucy Klebanow, wrote about what she described as a “nightmare” dinner in the 1970s. She recalled Trump arriving in a white Cadillac with a red interior and a car phone, a major flex at the time. But the date allegedly ended with Klebanow footing the bill when the restaurant didn’t accept credit cards and Trump didn’t have cash. According to her account, he promised repeatedly to pay her back. She says he never did.
Ivana Trump and the Marriage That Created a Power Couple
Then came the marriage that truly launched Trump into the power-couple stratosphere: Ivana Zelníčková. The two met in 1976, married in 1977, and built what looked like a glittering empire together. Ivana wasn’t just a trophy wife; she was deeply involved in the business, taking leadership roles in Trump properties. They had three children: Donald Jr., Eric, and Ivanka. But the fairy tale imploded amid reports of Trump’s affair with Marla Maples.
The divorce was explosive and deeply public. In a sworn deposition referenced in Lost Tycoon, Ivana accused Trump of sexual assault, though she later clarified she hadn’t meant it in a “literal or criminal sense.” The split reportedly ended with a $14 million settlement. Years later, Ivana described Trump as someone who “just says it as it is,” admitting, “Donald cannot be calm.” Despite everything, the two eventually rebuilt a cordial relationship, even speaking regularly during his presidency.
Marla Maples, Scandal, and a Tabloid-Fueled Divorce
Marla Maples, the woman at the center of that divorce storm, became Trump’s second wife. They married in 1993, shortly after the birth of their daughter, Tiffany. But the relationship was turbulent from the start. Maples later described their marriage as “built on an illusion” and called him “ego-driven.” After their divorce in 1999, she moved to California to raise Tiffany largely outside the spotlight, noting that while Trump was “a good provider,” the day-to-day parenting was primarily her responsibility.
Between marriages, Trump’s dating history reads like a 1990s tabloid fever dream. He was linked, sometimes confirmed, sometimes denied, to a string of models and celebrities. Argentinian tennis star Gabriela Sabatini was rumored to have dated him briefly. Carla Bruni publicly denied ever being his “new one” after he allegedly claimed she was. Ukrainian model Victoria Zdrok accused him of being “really into himself,” while Trump insisted he didn’t even know who she was.
Rumored Relationships and Celebrity Connections Over the Years
Some former flames spoke glowingly. Allison Giannini described him as “a great, great guy” who was “very gentlemanly.” Barbara Moore claimed he was “a great lover and a gentleman.” Rowanne Brewer Lane defended him against what she felt was unfair media coverage, calling him “a gentleman.”
But not all stories were flattering. The infamous 2005 Access Hollywood tape captured Trump boasting, “I don’t even wait. And when you’re a star, they let you do it.” During a 2016 debate, he dismissed the remarks as “locker room talk.” Meanwhile, Barry Levine and Monique El-Faizy’s book All the President’s Women detailed numerous allegations of inappropriate behavior claims Trump has denied.
Then there’s Stormy Daniels. According to Daniels, their alleged affair began shortly after Melania gave birth to Barron in 2006. Daniels later described their encounter in a televised interview, claiming she spanked him with a Forbes magazine. Trump has denied the affair and labeled the allegations “false and extortionist.” A nondisclosure agreement and hush money payment became central to legal and political drama that followed him into office.
Melania Trump and the Relationship That Reached the White House
Through it all, one woman has remained by his side: Melania Trump. They met in 1998 during Fashion Week. According to accounts, she declined to give him her number at first, flipping the script and asking for his instead. They married in 2005 in a lavish ceremony, with Melania wearing a Dior gown reportedly requiring 550 hours of labor and 1,500 crystals. “We are standing by each other and we are equal in the relationship,” she told Tatler.
Trump’s love life has been as high-profile and polarizing as his career. Admirers call him charismatic and magnetic. Critics see ego and controversy. The relationships have ranged from brief flings to headline-grabbing marriages, from affectionate testimonials to courtroom allegations.
Love him or loathe him, one thing is undeniable: Donald Trump’s romantic history has never been dull. It’s been dramatic, messy, glamorous, and controversial, a reflection of the larger-than-life persona he has carefully cultivated for decades. Like his politics, his personal life is one thing that people can’t seem to agree on.
Lola Wheeler 
Sofia Bassett 
Nina Franklin 
