Donald Trump's 19-Year-Old Son Reportedly Made a Romantic Gesture to His Date

A romantic evening in Manhattan involving the President's youngest son is quietly making waves because of what had to be arranged behind the scenes.

Barron Trump, the 19-year-old son of President Donald Trump and First Lady Melania Trump, was recently part of a carefully choreographed date night at Trump Tower. Though the college sophomore is navigating a new semester like any other student, even the smallest private moments and gestures take on a very different shape when you're part of a prominent family.

A Date Night

On September 29, 2025, Page Six reported that a source had witnessed Barron hosting a date at his father's iconic building in Manhattan. But the rendezvous wasn't your average outing. According to the insider, an entire floor was sealed off for the romantic evening for security reasons.

And yet, for the youngest member of the Trump dynasty, this level of precaution is not out of the ordinary.

Back in April, another source told Page Six that Barron wasn't even allowed to give out his phone number at school. Instead, he communicated with peers through Xbox and Discord, carefully sidestepping the risks that come with being the son of one of the most recognizable figures in the world.

The insider explained that giving out his phone number would be a disaster, as it would almost certainly leak, and his phone would never stop ringing.

Dating Rumors and Conflicting Reports

Buzz about Barron's dating life began circulating in May, when an alleged NYU friend told NewsNation that the teenager had a girlfriend and spent a great deal of time with her.

But despite the bold claim, no one else has confirmed it. Additionally, nearly a year ago, President Donald Trump appeared on Patrick Bet-David's podcast, commenting that he didn't believe Barron had a girlfriend at the time.

And this year, a People source echoed that sentiment, adding that dating wasn't a big part of the young man's life at the moment. "He has more school, a family who dotes on him and a career of his own he is launching," the source explained.

Many Campuses

Earlier this month, the New York Post reported that Barron had been living at the White House while attending classes at NYU's D.C. campus. He had been expected to return to the Greenwich Village location by September 2, but he didn't show.

People later confirmed that he would instead attend another campus, but officials refused to reveal which one at the time for security reasons. NYU has locations in Brooklyn, Abu Dhabi, and Shanghai, as well as other learning centers in Los Angeles and Washington, D.C.

The Business Side of Barron

Though he successfully completed his first year of college in May, Barron didn't spend his summer lounging at the beach. Instead, an insider told People he was traveling, staying at Trump properties, and quietly laying the groundwork for his future.

He has reportedly been meeting with business figures and exploring deals in the tech sector, with plans to launch his own company. Alongside his budding career, Barron also spent quality time with his family — a rare blend of presidential legacy and private ambition.