Ivanka Trump is always in the headlines. From details about her expensive outfits to her influence in the White House to her presence on the campaign trail, Ivanka has made a name for herself as the darling of the Republican party. And while she’s advised Donald Trump on policy, tweeted that Capitol rioters were “patriots,” and has been raising her children, Ivanka’s influence on the social circles she once belonged to has reportedly been dwindling.
As many know, the Trumps were once at the heart of the Manhattan elite — they rubbed shoulders with celebrities, owned the most opulent hotels, were spotted at major city events, and were the stars of The Apprentice. Indeed Ivanka greatly benefited from the spotlight, launching her own businesses and meeting her millionaire husband along the way.
But Ivanka’s charm and poise — very much the opposite of her father’s approach — hasn’t stopped people from sharing what they know about her. Most notably, journalist Lysandra Ohrstrom — Ivanka’s former best friend — wrote an in-depth article for Vanity Fair detailing the friendship they once shared, and subsequently how it fizzled out. So buckle in, because here’s everything that Ivanka Trump’s former best friend revealed.
Ivanka Trump was reportedly the Queen Bee in middle school
We can’t imagine that this comes as a shock to anyone who’s observed Ivanka Trump and her behavior in Washington, D.C., but Ivanka was the queen bee in middle school, according to journalist Lysandra Ohrstrom, her former best friend.
Ohrstrom wrote in Vanity Fair that she met Ivanka in the seventh grade at one of Manhattan’s premiere all-girls schools, Chapin — whose alumni includes Jackie Kennedy — and according to the writer, Ivanka ruled the halls. “After spending the previous four years in social isolation in the suburbs, I was eager to land on the popular side of the classroom, ruled over by Ivanka and about five other wild, entitled, precocious preteens,” Ohrstrom wrote. “It was the grunge era, so we moshed around the classroom in performative angst, wearing our uniforms of green plaid kilts (tailored shorter the more popular you got) and stacked-heel Steve Madden loafers as the dystopian wails of Nirvana blared from a boom box.”
We wonder who exactly was in Ivanka’s “squad” of reportedly entitled pre-teens, but we imagine that the group walking the halls looked very similar to the high school hallway montage from Mean Girls.
Donald Trump allegedly once asked if Ivanka Trump was the prettiest girl in school
Google “Donald Trump and Young Ivanka” and look at the photos — actually, don’t, as you might think it’s creepy. Still, you’ve probably seen the photos of a teenage Ivanka sitting on her father’s lap, and it’s clear that the, um, affection between them was a big part of her life growing up.
So much so that journalist Lysandra Ohrstrom confessed in her piece for Vanity Fair that The Donald once asked her if Ivanka was the prettiest girl school. “He would barely acknowledge me except to ask if Ivanka was the prettiest or the most popular girl in our grade,” Ivanka’s former best friend wrote. “Before I learned that the Trumps have no sense of humor about themselves, I remember answering honestly that she was probably in the top five.” And when Donald reportedly asked who could possibly be more attractive, he also allegedly described two other schoolgirls, saying one looked like Cindy Crawford and the other “had a great figure.”
Yeah… we’ll leave you to digest that. To top off an already awkward interaction, Ohrstrom claimed that Donald would “usually congratulate” her if she’d lost any weight.
After Ivanka Trump's wedding, the friendship between her and her best friend began to crumble
Ivanka Trump and Lysandra Ohrstrom were best friends for over ten years, their relationship described by Ohrstrom as “more sisters than best friends.”
However, eventually the connection between the two women began to crumble, and things seemed to bubble up to the surface around the time that Ivanka got married to Jared Kushner. “In 2009, shortly after I was one of two maids of honor in Ivanka’s wedding, our friendship finally broke under the weight of our differences,” Ohrstrom wrote in Vanity Fair. “When I started a new job in a different field the day after their wedding… I expected my best friend to ask how it was going.” But Ivanka reportedly never did, so Ohrstrom sent her a text a few weeks later. “[It] said something like, ‘Hey, I started a new job the day after your wedding, and you haven’t asked me a single question about it.'” Ouch.
Ohrstrom added that she didn’t exactly recall what Ivanka said in response, but it reportedly had the tone of “I don’t have time for this” — you know, how your closest friend talks to you.
Ivanka Trump reportedly had this reaction when her best friend brought up low-income families
Ivanka Trump and her father spent much of their D.C. years seemingly advocating for America’s working class. On the White House website, it lists the eldest Trump daughter as an advocate for “economic growth through workforce development.”
However, according to journalist Lysandra Ohrstrom’s article in Vanity Fair, Ivanka’s approach to people who’ve not been as fortunate as herself hasn’t always been sympathetic. “I had recently recommended Empire Falls, Richard Russo’s 2001 Pulitzer Prize–winning novel about the life of a diner manager in a working-class community in Maine,” Ivanka’s former best friend recalled. “‘Ly, why would you tell me to read a book about f**king poor people?’ I remember Ivanka saying. ‘What part of you thinks I would be interested in this?'” Talk about a different tone.
But this isn’t the first time Ivanka has been accused of being out of touch when it comes to working family issues — just remember the time that she wore a $2,110 dress while attending a White House event and posed with “American working families” (via Express). Then think about how much your rent is per month.
Did Ivanka Trump sacrifice the polished image she worked hard to create?
Donald Trump has been accused of having a temper — think of his banned social media accounts and the boisterousness of his rallies.
However, Ivanka Trump, for a while, had a different approach. As Lysandra Ohrstrom described, Ivanka brought “a more refined” sense to the Trump name, and wasn’t known for being so bombastic. But, according to Ohrstrom, times have changed. “When Ivanka joined her dad’s administration, I was sure she would step in to moderate her father’s most regressive, racist tendencies,” Ivanka’s former best friend wrote in Vanity Fair. “I’ve watched as Ivanka has laid waste to the image she worked so hard to build.” Ohrstrom added that she’s talked to many of Ivanka’s school friends about how “appalled we are that she didn’t publicly oppose… any of her dad’s especially repugnant policies.” However, they’ve all been publicly mum on the topic.
That’s arguably with good reason, as the fear of publicly criticizing a Trump is significant. The Trump White House had a steady revolving door of those who’d been hired and fired, and critics of the president and his family have largely been humiliated.
Growing up, teen Ivanka Trump was reportedly on the straight and narrow path
There never seems to be anything more exciting for a teenage girl than the allure of breaking the rules. However, while Ivanka Trump and her squad got away with a trip to Atlantic City, she was pretty much on the straight and narrow path growing up, according to journalist Lysandra Ohrstrom. “Most of us were allowed to roam freely around Manhattan above 57th Street by bus or taxi before dark,” Ivanka’s former best friend wrote in Vanity Fair. “Some of us even went to Sheep Meadow to ‘dye our hair green,’ which was the code used by the entire classroom in reference to a certain forbidden activity.”
While grunge may have been king at the time, Ohrstrom added that Ivanka and her crew were anything but, as they “not only lived in palatial townhouses or duplexes scattered between 60th and 64th streets between Fifth and Park, but retired to equally palatial country houses for the weekend.”
And if the lavish houses and the money wasn’t enough, Ohrstrom revealed that, while at Chapin, there was clearly a “pecking order.” This sounds like our worst nightmare.
Ivanka Trump and her father are apparently very similar
The saying goes “Like father, like daughter,” and that certainly seems to be the case for Donald Trump and his eldest daughter, Ivanka Trump. According to journalist Lysandra Ohrstrom’s piece in Vanity Fair, Ivanka started to communicate — while in her school days — that her teachers had never witnessed such talent. She reportedly always looked put together, “stopped at McDonald’s for cheeseburgers,” made a habit of swearing, and “had the Trump radar for status, money, and power, and her dad’s instinct to throw others under the bus to save herself,” as noted by Ivanka’s former best friend.
Of course, the close relationship between Ivanka and her father is not groundbreaking news, as The Donald has made it clear that Ivanka is his favorite child. As noted by The Atlantic, “Ivanka’s favorite-child status had long been tied to the good press she generated for her dad.” Additionally, for Donald, “everything comes back to optics,” former White House aide Cliff Sims explained. “She is the archetype of what he wants — the most beautiful face, the most buttoned-up message, everything just exactly the way it should be.”
Ivanka Trump reportedly used social standing to threaten her former best friend
Many people have a toxic best friend story, and for Lysandra Ohrstrom, that best friend was arguably Ivanka Trump. As she wrote in Vanity Fair, Ohrstrom indicated that Ivanka threatened her social standing, all while she was trying to navigate a tumultuous environment as a journalist. “While Ivanka was laying the foundation for her conquest of Manhattan, I was experiencing a new reality in Lebanon…,” Ivanka’s former best friend wrote, noting political upheaval. “During my first two-year stint in Beirut, Ivanka regularly emailed me messages like, ‘When are you getting your ass back to NYC? You’re going to be replaced.'” She added that Ivanka never asked her how she was dealing even during a literal war.
Now we don’t know if you’re dealing with a war, facing a personal crisis, or just trying to navigate this ridiculously insane world that we live in, but if you’re reminded of your own close friend while reading Ivanka’s answer to Ohrstrom, we have one piece of advice: drop them.
This allegedly became a sore topic for Ivanka and her best friend
Unless you’ve been living under a rock, you’ve heard the term “conflict in the Middle East” at some point. As noted by Lysandra Ohrstrom in Vanity Fair, the difference in perspectives between her and Ivanka Trump on the issue became a point of contention between them.
Ivanka famously converted to Judaism before marrying Jared Kushner, as noted by ABC News, and things subsequently got complicated for her and Ohrstrom. “She had started dating Jared Kushner, whose family was Orthodox Jewish, and my pro-Palestinian stance began to chafe,” Trump’s former best friend wrote. “Since 2007, I’ve worn a necklace with my name written in Arabic, and Ivanka grew increasingly irritated by it.” It came to a head one night when Ivanka chastised Ohrstrom for wearing the necklace, suggesting it might even be offensive to her boyfriend, who’s Jewish.
We truly don’t know how to respond to that. Maybe the takeaway from this is that no matter what, don’t speak to your supposed best friend like this? That seems obvious, but we guess it bears repeating.
Despite differences, Ivanka remained polite to her former bestie
The Trump family arguably loves to keep up appearances — or make it at least appear like everything’s fine. Just think of the times Melania Trump has gone viral for looking dismayed, or for swatting her husband’s hand away from hers, only to never say anything critical about him. That behavior pretty much shows that the Trumps always want to “look” the part.
That same mentality seemed to be Ivanka Trump’s approach to her former best friend, Lysandra Ohrstrom. Ohrstrom wrote in Vanity Fair that despite the differences between her and Ivanka — and the choice words that have been shared between them — Ivanka maintained appearances and made sure to send Ohrstrom gifts on her birthday; she even invited Ohrstrom to her birthday parties (yes, parties). “When my son was born, she sent me a gold-plated bracelet engraved with his name,” Ohrstrom wrote. “She was never impolite, but we no longer belonged to each other’s inner circles.”
Since Ivanka may have alienated herself from the Manhattan social scene (via The New York Times), we can only wonder who makes up her inner circle now.
Ivanka Trump's former best friend compared her to royalty
We shamelessly love the UK’s royal family, there’s no denying it. Any sighting of Prince William and Kate Middleton, count us in — we’ll be there. But Lysandra Ohrstrom describing Ivanka Trump and her family as “American royalty” doesn’t seem to have the same affectionate undertones as our unhinged love for the British royals, and you’ll quickly see why. “Ivanka had deigned to dress Middle American housewives when I knew her,” Ivanka’s former best friend wrote in Vanity Fair. “But aligning herself with her dad’s banana republic-style administration made no sense to me, until my friend suggested that Ivanka took her kids to the rally to show them that they are American royalty.” She added that it’s a decent observation, given the character of the Trump White House.
Of course, criticism of Ivanka and her family is not uncommon. Bess Levin of Vanity Fair described Ivanka as someone who “comes from a long line of a**holes who confuse inheriting money with hard work,” a figure who continues to make millions of dollars while “doing nothing.” Ouch.
Ivanka Trump reportedly wants to be re-accepted by the Manhattan social scene
New York City is one of the best places in the world, and Ivanka Trump grew up with the Big Apple at her fingertips. It’s no surprise, then, that she’s reportedly craving Manhattan society’s acceptance again.
However, the only problem, according to Ivanka’s former best friend Lysandra Ohrstrom, is that the New York scene allegedly doesn’t want her back. “I’ve been comforted by the certainty that the backlash from those whose respect she craves most must sting. Still, I miss my old friend,” Ohrstrom wrote in Vanity Fair. “I miss the time when the Trump family quest for power was not dangerous to the country.”
Ohrstrom also speculated that Ivanka will most likely find a new home in Palm Beach, where she estimated that “most misdeeds are forgiven if you have enough money.” And it looks as though other members of the Trump family will retreat to Florida to “lie low” after the chaos that’s ensnared Washington, D.C. According to People, Melania Trump was spotted in Florida in December 2020, checking out potential schools for her son, Barron Trump.
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