Awkward Tiffany Trump Moments That Were Witnessed By Millions

Former president Donald Trump has five children with three different women. During his first marriage to socialite Ivana Trump, Donald fathered two sons, Donald Trump Jr. and Eric Trump, as well as one daughter, Ivanka Trump. In his most recent marriage to model, Melania Trump, the ex-president welcomed a son called Barron Trump. And during his brief second marriage to Marla Maples in the '90s, Donald had a daughter named Tiffany Trump.

In contrast to most of the Trump children, who grew up in Manhattan, Tiffany spent much of her childhood in California with her mom. As Maples told People in an interview, "Her daddy is a good provider with education and such, but as far as time, it was just me." To this, Tiffany added, "She [Maples] moved us out of New York to get out of the spotlight and let me grow up and find my own identity versus being in the shadow of a name."

When the 2016 elections came rolling around, though, Tiffany found that there was no way of avoiding the weight of her famous last name. She had little choice but to be thrust into the spotlight. Eventually, she decided to join the Trump cause. Since her father's first bid for the presidency, Tiffany has joined him at numerous public and media events. This level of exposure has, of course, landed her in a number of awkward public situations — many of which have been downright humiliating.

These days, Tiffany Trump's social media is full of photos from her father's political campaigns. However, long before she was associated with any sort of presidential run, Tiffany was just an undergrad at the University of Pennsylvania. During her time at school, Tiffany seemed to be a pretty typical student — at least in some ways. Her Instagram was plastered with photos of the library, late-night pizza, and nights out on the town. One particular post even showed the heiress attempting to model, but the clip wasn't received well online.

In 2015, the youngest Trump daughter shared behind-the-scenes footage of a photoshoot for Just Drew — a fashion line that had been launched by Andrew Warren. In the video, Tiffany joined Warren and three other media personalities as they awkwardly danced on set while a photographer snapped photos. Although the participants seemed to be having fun, they didn't seem particularly comfortable prancing around to get the perfect shot.

Naturally, Tiffany's followers noticed a hint of awkwardness in the video, and many were quick to point it out. "Oh my gosh this made me feel so embarrassed," posted one user, who went on to add, "You can't move at all." Another described it as, "The funniest and most uncomfortable thing I ever saw on Instagram." A final user summed things up in two words: "So cringey." 

In 2016, Tiffany Trump's life changed forever when her father Donald Trump decided to run for president of the United States. Up until that point, Tiffany had been a relatively unknown university student. However, when her father cinched the Republican nomination, she found herself wrapped up in a hurricane of campaigns.

This was apparent during that year's Republican National Convention (RNC), where Tiffany was invited to give a speech on behalf of her dad. Standing in front of an enormous audience in Cleveland, Ohio, Tiffany spoke highly of Donald's role in her upbringing. As she applauded her dad for reading her report cards in elementary school, Tiffany's enunciation was clear, and her posture appeared confident. That being said, there were moments when her lack of public speaking experience shone through — one of those being her comparison between the RNC speech and classroom presentations.

"Please excuse me if I'm a little nervous," she said shortly after taking the floor (via CNN). "When I graduated college a couple of months ago, I never expected to be here tonight addressing the nation. I've given a few speeches in front of classrooms of students, but never in an arena with more than 10 million people watching." Although this comment was meant to be a joke, it did not get a lot of laughs. Instead, it made for an uncomfortable moment.

Although Tiffany Trump's first RNC speech was shaky, she seemed to grow increasingly confident over time. As she attended more and more events, Tiffany appeared at ease in front of the cameras. That being said, she has not always presented as comfortable around her father.

Speaking about Tiffany's relationship with Donald Trump, a source anonymously told People, "They always had a strained relationship her whole life." Perhaps, then, it was for this reason that Tiffany seemed surprised when Donald approached her for a kiss on the cheek following the second presidential debate in 2016. A video of the moment captured Donald leaning toward Tiffany, causing her to immediately lunge backward. Although this moment was clearly awkward, the youngest Trump daughter seemed to recover quickly and gave her dad a friendly pat on the shoulder instead.

All rumors aside, Tiffany has long insisted that she and her father are not as uncomfortable around each other as they may seem. As she told People, "I really have an emotional bond with him and he was always just the funniest, most loving father. I'm so lucky to have parents who are so supportive of me." In that sense, it is possible that Tiffany and Donald's failed cheek peck at the RNC was just an issue of poor timing and not proof of a strained relationship between Donald Trump and his daughter.

As Tiffany Trump became more and more involved in Donald Trump's political goals, she gained an increasing number of responsibilities. During the 2020 elections, she campaigned for her father — even speaking on his behalf at a Trump Pride event in Tampa, Florida. Standing before the podium in front of crowds of potential voters, Tiffany claimed that Donald was a huge supporter of the LGBTQ+ community. "I'm here because I support my father. He supports all of you," she said (via NBC News). As enthusiastic as Tiffany sounded, her words were not as well-received as the Trump campaign evidently hoped.

Throughout the speech, Tiffany looked nervous in front of her audience. At one point, she blurted, "I'm here speaking. I wouldn't lie to you. I promise." Unfortunately for Tiffany, this impromptu declaration did make it seem like she was lying.

To make matters worse, Vanity Fair published a piece cautioning the public to take Tiffany's speech with a grain of salt. Although Donald had claimed support for LBGTQ+ marriage during his previous campaigns, his administration was not fully accepting of the queer community. As reported by the outlet, the Trump administration eliminated previous legislation that had once protected LBGTQ+ folks in spheres ranging from health care to adoption to schooling to employment. The former president also reportedly appointed a number of judges with proven anti-LBGTQ+ bias. 

The pride presentation was not the only time Tiffany Trump gave a speech that was not well-received. At the 2020 RNC, she gave an address that included a pretty bizarre comment about her employment status. In a clip that was later shared to X, formerly Twitter, Tiffany declared, "Like so many students across the world, I graduated from law school during the pandemic. Our generation is unified in the facing [sic] the future in uncertain times ... As a recent graduate, I can relate to so many of you who might be looking for a job."

Tiffany Trump's full remarks at the @GOPconvention#RNC2020 pic.twitter.com/sNz0xNPEEE

— Team Trump (Text TRUMP to 88022) (@TeamTrump) August 26, 2020

Unfortunately for Tiffany, these words came back to haunt her. Critics were quick to point out that she cannot relate to most Americans — including recent college grads. The reason? She is the daughter of a billionaire.

In reality, Tiffany Trump lives an extremely lavish life that includes yachting in the Mediterranean, summering in the Hamptons, and rubbing shoulders with celebrities, like Lindsay Lohan. For most Americans, securing employment is a matter of survival. For Tiffany, this is clearly not the case. When she graduated from law school, the youngest Trump daughter got a job as a research assistant at Georgetown University Law Center — a position that could never pay for her over-the-top lifestyle.

The Trump family politics are notoriously complicated. Ivanka Trump and Melania Trump are rumored to have a rift. Eric Trump and Donald Trump Jr. might have a bit of a rivalry. And, Tiffany Trump is said to have a more distant relationship with the rest of her siblings.

This sense of isolation is believed to have grown more intense in 2024, as Tiffany has apparently lost status within Donald Trump's campaign. This was evident at that year's RNC — because Tiffany was not asked to give a speech at the convention for the first time since her father went into politics. Rather than invite Tiffany to take the podium and speak on his behalf, Donald gave his daughter a small acknowledgment in his speech. Per footage shared by Forbes, the former president said, "I also want to thank my entire family for being here. Don and Kimberly, Ivanka and Jared, Eric and Lara, Tiffany and Michael, Barron. We all love Barron."

Although this acknowledgment may seem friendly, it represents a huge step down from the honor that Tiffany had received at previous RNCs. Adding insult to injury, the Trump campaign asked Donald's 17-year-old granddaughter Kai Trump to take the podium at the event. In other words, it appeared that Tiffany was upstaged by her much younger niece.

Donald and Tiffany Trump had an exchange at the 2024 RNC that made her seem like an afterthought to the former president. The trouble presumably started when Donald wandered into the audience as his family were taking their seats. 

As Tiffany approached her father and flashed him a friendly smile, Donald turned away, literally giving her the cold shoulder and focused his gaze elsewhere. This gesture — while small — seemed quite significant from Tiffany's perspective. It instantly wiped the smile off her face, creating a tense moment.

Trump shades his Christian daughter Tiffany Trump at the RNC in Milwaukee.

Follow:@NoticeNewsNet pic.twitter.com/MOEvOstoRC

— Noticing News Network 🇺🇸 (@NoticeNewsNet) July 29, 2024

In what appeared to be an attempt to recover, Tiffany gave her father an air kiss to the back of the head before walking away. Tiffany's husband, real estate billionaire Michael Boulos, however, did not seem so smooth in his exit. As he walked past his father-in-law, Boulos stared at the back of his head uncertainly. At one point, he hesitated slightly, as if wondering whether or not to greet the former president. In the end, though, Boulos copied his wife and carried on — taking Donald's snub in his stride.