Former President Donald Trump is no stranger to exaggeration. However
unlike Trump's many baseless brags, his reputation as a ladies' man apparently is rooted in truth
From his teenage dates to his marriage with Melania, here's a peek inside the divisive businessman's complicated love life
In an interview with Harry Connick Jr. on his now-defunct talk show
Candace Bergen admitted to going on a dinner date with Donald Trump
Bergen shared that she was 18 years old at the time and studying at the same college Trump went
on to attend. She said, "'It was like a blind date. He called me in the dorm and I was bored. So he picked me up
He was wearing a burgundy three-piece suit with burgundy patent leather boots and he was in a
burgundy limousine. So it was very color-coordinated.'" Evidently, Bergen wasn't a big fan of head-to-toe
claret-colored clothing and cars, as she said she got home by 9 p.m. after a short dinner
Bergen revisited the subject during a Watch What Happens Live segment in 2017 called
Candidly Candace. When pressed by host Andy Cohen on whether she gelled with the Venn teenage Trump
Bergen insisted there was no chemistry between them. She doubled down by asserting that they
had no physical contact at all. Cohen persisted, though, asking Bergen if she found Trump to be attractive
He was a handsome, he was a good-looking guy. Yeah. And a douche
Kim Richards started out her career in show business as a child star, appearing in movies
such as Escape to Witch Mountain and TV series like The Wonderful World of Disney. Years later
she would find success in the world of reality TV when she was brought on as a member of the
original cast of The Real Housewives of Beverly Hills. After a few tumultuous seasons
she parted ways with her spot in the main roster, but has continued to make guest appearances on the
show over the years. One of her most memorable moments? Why, that would be when she dropped by
the Season 7 reunion and revealed she used to date the 45th president. Host Andy Cohen asked
Richards to confirm a rumor that she once dated Trump. Is that true
Yes. While the other housewives wanted more details, Richards would only share that they went out to dinner
I don't want to talk about the president. Oh, come on. Donald Trump met Ivana in 1976 when he spotted her waiting outside a Manhattan restaurant
The 30-year-old swooped in and secured a table for the 27-year-old Czech model and her friends
A year later, they were married in a secret private ceremony. The couple worked tirelessly to expand Donald Trump's empire
As Vanity Fair reported in 1988, Ivana took an active role, first as the vice president
of Interior Design, and then as CEO of Trump's Castle Casino in Atlantic City
They had three children together — Donald Jr., Eric, and Ivanka. We get along very well, and there's not a lot of disagreement
because ultimately, Ivana does exactly as I tell her to do. As the New York Times noted, four different prenups were renegotiated as their family and
wealth grew. But their marriage exploded after Ivana discovered Donald had been cheating on
her with Marla Maples. He's not a chauvinist, is he? Oh, he's the worst
A humiliating and very public showdown between mistress and wife on the ski slopes of Aspen
instantly sparked a tabloid frenzy. The affair was front-page news as Donald and Ivana duked it
out in a bitter divorce battle. In Lost Tycoon, The Many Lives of Donald J. Trump, author Harry
Hurt III writes that in a sworn deposition, Ivana accused Donald of sexual assault. But in a statement
for the book, Ivana insisted she hadn't meant rape in, quote, a literal or criminal sense
The couple finally agreed on a $14 million settlement in 1992. Still, the fallout would
continue. Ivana Trump wrote in her own memoir that Donald Jr. reportedly refused to talk to
his dad for a year. It took time for the wounds to heal and for them both to put their bitter
divorce behind them. However, Donald and Ivana Trump did manage to eventually make up
Donald Jr. also managed to forgive his father's transgressions and join the family business
alongside siblings Eric and Ivanka. Since then, Ivana has become a close confidant of Donald's
She told the New York Post in 2016, "... we speak before and after the appearances and he asks me what I thought.
These days, Ivana manages to always keep it real and speak her mind, just like her vocally
forthright ex, but it would appear that her advice often falls on deaf ears
such as when she suggested to Donald that he calm down his rhetoric a notch or two
She told The Post, Donald Trump may not heed his first wife's advice
but he clearly still respects Ivana's business savvy, so much so that after he became president, he offered her the position of Czech ambassador
In a different interview in 2017, she told The Post, My ex said
Ivana, if you want it, I give it to you. However, she declined the offer, explaining
I like my freedom and I want to do what I want to do. Go wherever I want to go with whomever I want
I don't need the prestige. And it's an 8 to 12 job. The tabloids poured over every detail of Donald and Ivana Trump's divorce battle
There was an endless stream of salacious stories about Donald Trump's then-still-unconfirmed
affair with Marla Maples. It's hot. It's pretty hot. There was also a seemingly limitless list of beautiful women that the self-professed playboy
was romantically linked to. Katherine Oxenberg was one of them. In a twist of faith, the Dynasty
star twice portrayed Princess Diana, whom the Donald was apparently very into. According to a
report in the Sunday Times, Donald apparently sent Diana flowers after her divorce, believing she was
quote, the ultimate trophy wife. The report went on to note that Diana had zero desire to become
the next ex-Mrs. Trump, and neither did Oxenberg, who shot down the dating rumors, telling People Magazine
It's a complete joke as far as I'm concerned. I hardly know the man. A tipster told the outlet
that Donald and Oxenberg were platonic pals. Donald Trump and Marla Maples first bumped into each other on Madison Avenue after he ditched his glimo and walk to work instead Maples told Vanity Fair had seen him at different places throughout the years I was just somebody he shook hands with
They immediately became firm, but platonic friends, Marla insisted. But as Vanity Fair
recounted, this eventually moved to the next level as Maples started appearing on his arm
all over Atlantic City, pretty indiscreet, given that Donald's then-wife, Ivana Trump
was CEO of Atlantic City's Trump Castle. Nonetheless, it took another year before
Ivana learned of the affair. Ivana wrote in Raising Trump, Still, Donald attempted to keep his relationship with Maples on the down low while his divorce
from Ivana played out. Their affair was tumultuous, with multiple breakups. However
things seemingly settled down — for a while, at least. Donald and Maples married in 1993
two months after the birth of their daughter, Tiffany Trump. They separated just four years
later, and by 1999, they were officially divorced. Maples didn't hold back when it came to talking
about her egotistical ex. She told the Daily Telegraph that Donald had been obsessed with her
and that their marriage was, quote, built on an illusion. Unlike Ivana, who walked away with $14 million and $650,000 a year in child support
Maples had to make do with $2 million following her failed marriage
Donald also agreed to pay $100,000 a year child support until Tiffany Trump turned 21
A source told Vanity Fair that Maples, quote, was out of her depth in Trump's world. The source went on to add
"'It's a sad story. She really didn't know how to handle him.'
Maples admitted to the Telegraph, "'Donald was never the man I wanted to marry. He and his world were alien to me
I'm so happy to be away from Donald. And I'm just trying to move as far away as I can.'
A spokesperson later insisted Maples' comments had been taken out of context
Still, there's no escaping that Maples pulled up stakes and moved over 2,800 miles away from
Donald to pursue a private life as a single mom in California. She told People
That was my choice, raising Tiffany outside of the spotlight. Her daddy is a good provider
with education and such, but as far as time, it was just me. Her father wasn't able to be
there with day-to-day skills as a parent. Donald Trump's relationship history is as
dramatic and erratic as his now-defunct Twitter feed. His complicated love life is like a tangled
ball of thread, with marriages, affairs, and flings all intertwined. However, the list of
women he's reportedly been involved with is as factually questionable as the estimated more than
30,000 false or misleading claims that The Washington Post counted during his presidency
Have you ever dated a playmate? I refuse to answer that question. On the grounds that it may be true? It may be true
One of the women Donald was supposedly romantically linked to is Argentinian tennis
star Gabriella Sabatini. The business tycoon reportedly dated the athlete for a month back
in 1989. Sabatini was 19 years old when she is rumored to have connected with the 43-year-old
Donald Trump. The beautiful brunette was at the top of her game, having just won a silver medal
at the 1988 Soul Games before reaching the semifinals in the Australian Open
Sabatini declined to acknowledge, let alone comment, on the dating reports at the time
but she supposedly denied having any relationship with Donald Trump to a Los Angeles reporter in 2019
Carla Bruni found herself at the center of a Donald Trump love triangle in 1991
after the New York Post exclusively reported that Trump had dumped Marla Maples for the singer
Trump acknowledged the story himself the day after the report dropped, telling the New York Post that Bruni was his new woman
Bruni was fresh out of a tumultuous affair with Mick Jagger, which Jerry Hall reportedly blamed as the catalyst for their separation
So Bruni probably wasn't chomping at the bit to be branded the other woman again
Bruni denied Trump's claims, telling the Daily Mail in an interview later that year that Trump
was a lunatic, then adding, It's so untrue, and I'm deeply embarrassed by it all. I've only ever met him once
about a year ago, at a big charity party in New York." However, in Mick, the Wildlife and Mad Genius of Jagger, author Christopher Anderson claimed
Bruni and Trump did hook up. He alleged she promised to split from Jagger if Trump left
Maples. Anderson quoted Trump as saying, "'She was trying to get me to leave Marla, something I had in mind anyway
and she was using every psychological trick in the book. Adding a further twist to the tale, though, in his 2017 biography, Lost Tycoon
Harry Hurt III insists Trump did invent the dating rumor, and was even the anonymous source behind the original story
Rowan Brewer-Lane told The New York Times in 2016 that she met Donald Trump at a Mar-a-Lago
pool party in 1990 when she was in her early 20s. Brewer-Lane said in the interview
he brought me out to the pool and said, that is a stunning Trump girl, isn't it
The newspaper went on to describe the incident as, quote, a debasing face-to-face encounter between Mr. Trump and a young woman he hardly knew
But Brewer Lane, who ended up dating Donald for a few months in 1993
disputed how her account was framed, saying, Basically, they lied to me
They promised me multiple times that it would not be a hit piece
And clearly it was? Brewer Lane's criticism of the piece made her a media sensation, and she appeared on
CNN, Fox & Friends, and other channels to complain about the Times article
They misled me. Playmate Barbara Moore claims she had an affair with Donald Trump from March to September 1993
when Trump was awaiting the birth of his fourth child. She told the Daily Mail
He was a great lover and a gentleman. I didn't know he was with someone else, let alone engaged
to Marla Maples, and it was only recently I learned she was pregnant at the time.
Moore met Trump during a Playboy fashion show at his Atlantic City Castle Casino Hotel The centerfold model was psyched to see Trump who had just released The Art of the Deal and become a celebrated Manhattan property tycoon Moore told the Mail
he's a powerful man, and he was one of the most eligible bachelors in the world
Moore says she went to a private cocktail party after the show. According to Moore
Trump only had eyes for her. After telling the 24-year-old she was beautiful and classy
they headed off to his suite for a night of something or other
Marla Maples was hoodwinked yet again after Donald Trump supposedly did her dirty in 1995
when unconfirmed reports began swirling that Trump was having an affair with New Zealand
supermodel Kylie Bax. Neither Trump nor Bax denied or confirmed the reports
deciding instead to plead the fifth. Still, they've maintained a close relationship over the years
Bax is a staunch Trump supporter, leaping to Donald's defense as he battled accusations
of misogyny during his presidential run. Multiple women went public with sexual harassment
and assault allegations against Trump, but Bax believed they were just seeking their
five minutes of fame. She also made light of Trump's infamous acts as Hollywood tape
She told NZME, I'm sorry, but he is a man. What about the 300 emails that Hillary Clinton has tried to cover up
What is more important, a guy trying to get a date or national security? It's unfortunate that
he has said these things, and things have been done. But how much has been blown out of proportion
and how much is true? As Inside Edition recounted in 2016, Alison Giannini dated Donald Trump just after his final breakup with Marla Maples
Giannini was 27 when she was set up on a blind date with the 50-year-old self-professed
multimillionaire. Despite only going out three times, Trump managed to impress Giannini
I know there have been a lot of things that have been said about him, but to me, he was just a great, great guy
While the two went their separate ways, Giannini bears no hard feelings
I really think he has a very sweet side to him that a lot of people don't see. Despite the briefness of their encounter, Trump left a lasting impression
spurring Giannini to launch a new career as a realtor. He always said, you know, real estate in California is always going to go up into buy real estate
and that's what I've done. Donald Trump may have had a thing with Jackie Siegel, star of Queen of Versailles and repeat
Below Deck guest. While chatting with HuffPost to promote the documentary in 2013
she shared that she once had a brief romantic relationship with Trump. Siegel said
We just went out a couple times. Like, he invited us to Mar-a-Lago and go to his parties and things
like that. He's a really great person. So much charisma." The socialite quickly backpedaled on her comments, though, telling the Orlando Sentinel
We're friends. I wasn't really dating. When I was modeling, I was on the Trump float in some parade
I can't believe there are headlines out there. Oh my God, how embarrassing
However, Jackie's husband, David Siegel, wasn't so shy about his affections for Trump
Following Trump's 2016 presidential win, the Timeshare mogul gushed to the Sentinel
"...it's the greatest thing that's happened to me since I discovered sex. In the next four years
we're gonna dwarf what we've done. I'll go out on a limb financially to grow this company.
And it seems Trump was committed to helping his buddy achieve his financial aims
Four companies linked to multimillionaire Siegel were approved for almost $18 million
in Paycheck Protection Program loans, which were supposedly created to help small businesses
stay afloat during the COVID-19 crisis, according to the Miami Herald. Donald Trump was once a Howard Stern Show regular, adding more shock to Stern's already
notoriously outrageous broadcasts. Trump was the king of TMI and making decidedly
inappropriate comments. He was an open book. Trump really managed to excel during a bizarre interaction in 2001
Stern was interviewing tabloid journalist A.J. Benza about his book, which includes a passage
about his girlfriend Kara Young dumping him for Trump. Not surprisingly, Trump just had
to add his 10 cents and promptly ring into the show. Trump said
I've been successful with your girlfriend. I'll tell you that, A.J. I won your girlfriend
You know it, she knows it, and everybody knows it." The two started hurling angry barbs at each other, kicking off with Benza slamming Trump's
hair and claiming he was out of his mind. Trump retaliated, alleging
"...AJ doesn't like Trump for one reason. I stole his girlfriend. I took her away like she was a dog.
And Trump wasn't finished there. After Benza threatened to bash his head in with a bat, he said
"...any girl you have, I can take from you." The story of Donald Trump and Victoria Zadrak boils down to a case of he said, she said
The Ukrainian model claimed in 2004 she went on four dates with Trump
However, he denied going out with her, telling celebrity journalist Chauncey Hayden
I don't even know who the hell she is. In an interview for Hayden's magazine, Steppin' Out, Zadrak alleged to Hayden that they met
after Trump badgered Playboy magazine to arrange a date between them. She added
He's really into himself. On a date, all he does is talk about himself
He loves himself. I went to an Ivy League school. I'm very highly educated
I know words. I have the best words." In a phone call obtained by the Daily Beast, Trump asks Hayden not to run the interview
In the audio, Trump insists he would have never dated the ex-penthouse pet, saying
She looks like a third-rate hooker. Zadrak herself wasn't complimentary, telling Hayden
"'I never met a more narcissistic person than Donald.'" She said that Trump loves to boast about his abilities as a lover
She also called Trump racist and commented on his hair, saying, "'He uses so much hairspray, I would never dream of touching it
But he doesn't care. He really thinks he's one of the most handsome people on Earth.'
Jill Hearth first encountered Donald Trump in 1992, when she and her boyfriend George
Torany met with him to discuss investing in their business. As noted in a New York Times feature, Trump was more interested in Hearth than in doing deals
Nonetheless he eventually agreed and in 1993 the couple flew down to Mar to celebrate Hearth filed a sexual harassment lawsuit in 1997 claiming Trump repeatedly groped her
One incident allegedly occurred in his daughter Ivanka's bedroom. She told The New York Times
"'I was admiring the decoration, and next thing I know, he's pushing me against a wall
and has his hands all over me.'" However, they continued to work together until Trump had a change of heart, and allegedly
They refused to pay the couple. Horany sued for breach of contract while Hearth filed her sexual harassment lawsuit, which
also alleged attempted rape. She eventually dropped the suit after Trump settled with Horany
Hearth and Horany married and then quickly divorced. Hearth told The New York Times that, in 1998, as she struggled to rebuild her life, Trump
who had just separated from Marla Maples, launched a charm offensive. and Trump actually dated for a while before he went on to marry Melania
Hearth's lawsuit was unearthed after Trump launched his presidential campaign. In 1996, the National Enquirer claimed that Trump told a friend
The truth is that Jill Hearth is obsessed with me and would do everything she could to get into my pants
Donald and Melania Trump first met in September 1998, when she snagged the attention of the mogul at a Fashion Week event
Vanity Fair reported that Donald was there with a date, but that didn't stop the 52-year-old from hitting on 28-year-old Melania
Donald asked the Slovenian model for her number, but she wouldn't provide it
instead insisting that he hand his digits over to her. Not before long, they went on their first date, Melania told Harper's Bazaar
I remember that night like it was two months ago. Nonetheless, as a friend of Melania told GQ
Early into their budding relationship, the couple split. However, they soon reunited
and in 2005 they wed in an over-the-top ceremony at Mar-a-Lago, Melania wearing a $100,000
dress bedazzled with 1,500 crystals. Melania told Tattler the year they married
"...we are standing by each other and we are equal in the relationship
And we support each other, you know? We always believe, both of us
woman behind a man and man behind a woman. One of Donald and Melania Trump's many marital
challenges occurred courtesy of Karen McDougal. The playmate alleged she had an affair with Donald
starting June 2006, three months after the birth of his son, Barron Trump. McDougal wrote about the
purported affair in a journal that was leaked to The New Yorker. She claimed she met Donald Trump
at a Playboy party, writing, "...he immediately took a liking to me, kept talking to me, telling me how beautiful I was.
They began chatting on the phone before arranging to meet at the Beverly Hills Hotel
After some talk, they hooked up, McDougal wrote. They allegedly continued to meet whenever Trump
was in Los Angeles or at multiple events around the country. McDougal claimed the guilt became
too much eventually, and she ended things in April 2007. Just days before the 2016 presidential
election, the Wall Street Journal broke the news of the alleged affair. The newspaper reported that
McDougal had been hushed up by the National Enquirer's parent company. At the time, American
Media was owned by David Pecker, a close buddy of Donald's. The company was accused of paying
McDougal for the rights to her story, preventing her from speaking about it ever again. Then
refusing to publish it. Both the media company and Trump denied all allegations against them
In 2006, Donald Trump also is alleged to have had an affair with Stormy Daniels
The adult film actor claimed their trist began four months after Melania Trump gave birth to
Barron, just weeks into Donald's alleged affair with Karen McDougal. Rumors about Donald Trump
and Stormy Daniels first surfaced on the blog The Dirty in 2011. At the time, Donald was just a
Manhattan property tycoon and reality TV star, so the story more or less flew under the radar
However, everything changed during Donald's presidential campaign. Daniels told 60 Minutes that 11 days before the election, she was persuaded to sign a $130,000
non-disclosure contract. Donald's attorney, Michael Cohen, brokered the deal. paying Daniels through a Delaware-based LLC created a month prior. By the terms of the
agreement, Daniels would be forced to pay $1 million each time she spoke about the alleged
affair, with a maximum penalty of $20 million. But Daniels refused to be silenced. In August
2018, she sat down with Anderson Cooper of 60 Minutes to dish the dirt. Trump denied the affair
and according to the BBC, called Daniels' allegations false, saying she was trying to extort him
Given all the scandals, sexual assault claims, and extramarital affair allegations, it's little surprise that speculation over the present-day Trump's future together has been rife
According to The Washington Post, gamblers started taking bets on a possible divorce before the 2020
election. The odds began decreasing as the end of Donald Trump's presidency drew closer
following his loss to Joe Biden. However, when Melania Trump's chief of staff
Stephanie Grisham, was asked about the split speculation, she shot it down, saying
This question is pathetic and exactly why people no longer trust the mainstream media
No legitimate journalist would ask this. Ex-White House official Omarosa Manigault Newman believes
otherwise, though. Newman wrote in Unhinged, an insider's account of the Trump White House
"...in my opinion, Melania is counting every minute until he is out of office and she can
divorce him. If Melania were to try to pull the ultimate humiliation and leave while he's in office
he would find a way to punish her." One thing's for sure, whatever Melania ultimately decides to do, her son will be at the heart of her
decision. Melania's former friend Stephanie Winston-Wolkoff claims Barron Trump's financial future is Melania's primary concern. Winston-Wolkoff alleges that the former first lady stayed
in New York during the first months of Donald Trump's presidency to renegotiate their prenup
guaranteeing Barron an equal share in the family business