Donald Trump’s Son Barron Is a ‘Ladies Man’ – 7 Photos of His Alleged Ex-Girlfriend Revealed #3

He spent high school out of the spotlight — no social media, no yearbook photos, and agents by his side. But now, Barron Trump is stepping into a new chapter. As he earns attention in college for his charm, a former classmate has surfaced with photos and claims of a past relationship.

Barron Trump reportedly spent his high school years keeping to himself, skipping school dances, and staying off social media. However, that’s changed in college. Now a student in New York, the teenager is reportedly well-liked on campus — and even considered a “ladies man.”

This follows the news that a former classmate of his came forward with claims of being Barron’s ex-girlfriend. See the images of the blonde beauty and what she had to say about their early connection.

Barron Trump’s High School Years and College Life

Before the buzz and the headlines about his love life, Barron lived a tightly guarded and surprisingly quiet existence inside the gates of Oxbridge Academy — an elite private school in Palm Beach, Florida.

As the only child of Donald and Melania and the youngest son of the U.S. president, his high school experience was anything but typical.

According to sources familiar with his time at the school, Barron didn’t just have classmates — he had bodyguards. Secret Service agents reportedly followed him across campus, waited outside classrooms, and even escorted him to the bathroom.

Furthermore, his name didn’t appear in any yearbooks, and he was registered in the school’s records under the alias “Jack” to prevent data leaks or grade exposure.

Teachers and classmates all knew him as Barron, though the name Jack occasionally drew confused glances during roll call — especially from substitutes.

Despite the restrictions, Barron left an impression. Former classmates described him as charismatic and impeccably well-behaved. One student shared:

“Barron was very funny and sociable. He would start the most random conversations and could be very entertaining.”

He was also viewed as a bit of a mystery — someone who didn’t attend school dances or join in on football games. “I don’t think he met up with anyone outside of school or went on dates,” the same source added. “If he had a girlfriend, it was top secret. We never knew about it.”

Melania, known for her privacy and protectiveness over her son, reportedly insisted that Barron stay off social media altogether. As a result, his image never surfaced online from school functions.

Rumors once swirled that he appeared in the background of a glitzy Monte Carlo–themed dance, but friends confirmed it was a case of mistaken identity. However, while Barron may not have immersed himself in the typical high school social scene, he did find his own rhythm.

He enjoyed playing the video game Clash of Clans and was known to be passionate about soccer. In fact, his father once shared a lighthearted anecdote. The president recalled:

“I said, ‘You’re gonna be a basketball player.’ He said, ‘Well I like soccer, Dad, actually.’ I thought, ‘At your height, I like basketball better.’ But you can’t talk them into everything.”

Barron even once met Premier League star Wayne Rooney at the White House and was photographed wearing an Arsenal kit — a subtle nod to his favorite club.

While he didn’t play sports at school, his interests did lean toward academics and aviation. He reportedly excelled in science and took on a mix of honors and honors seminar classes, the most advanced courses available at Oxbridge.

Standing at six feet and seven inches tall, he easily towered over his classmates and teachers — a quiet figure who blended in despite his commanding presence.

Barron often completed half his coursework online. When he did show up for in-person classes, his black SUV would pull into the campus around 8:30 a.m., just as the halls were emptying.

At lunch, he regularly joined friends in the cafeteria — but allegedly never ate. “He never specifically said why, just that he would wait until he got home to eat,” one peer recalled. “It was a little unusual.”

If he had a social life, classmates said, it happened outside school hours and away from his peers. There were whispers of events at Mar-a-Lago, such as a football banquet, but no clear signs that Barron mingled much.

“I don’t think he came downstairs or socialized with anyone,” said one source. Still, many of his classmates expressed pride in having attended school with him.

“A lot of the students consider themselves Republicans, and everyone was super excited when Trump showed up for graduation,” someone else revealed.

The reserved, enigmatic teen from Oxbridge had entered a new chapter — one where he no longer blended into the background, but instead, turned heads.

In May 2024, Barron graduated with his class, joined by his parents at the ceremony. In the months following his graduation, speculation swirled about where Barron would head next.

In August, his father offered a hint during a campaign stop, revealing that Barron was bound for a university in New York. Though Donald declined to confirm the name, he praised his son as a smart and capable student.

The mystery didn’t last long, though. By early September, Barron was photographed arriving on campus at New York University.

He had officially joined the freshman class at the Stern School of Business — one of the country’s most selective undergraduate business programs, known for its competitive admissions and academic rigor. By December, word had gotten out — Barron was settling into college life just fine. A source shared:

“He’s a ladies’ man for sure. He’s tall and handsome. A lot of people seem to think he’s pretty attractive — yes, even liberal people like him.”

The reserved, enigmatic teen from Oxbridge had entered a new chapter — one where he no longer blended into the background, but instead, turned heads.

With Barron enjoying college life, his mother spoke candidly about her experience of becoming an empty nester, saying, “We have them till they are like 18, 19 years old. We teach them, we guide them. And then we give them the wings to fly.”

A TikTok user named Maddie, known by her handle @maddatitude, claimed to be his former girlfriend — and brought receipts to back it up.

She added that she respected her son’s choices — where he wanted to go, what he wanted to do — and trusted him to chart his own course. And so he has.

From being “Jack” in the school computer system to becoming a young man quietly making waves at one of America’s most prestigious universities, Barron is stepping out.

The boy who lived in a guarded bubble is now a young adult with admirers, rumors, and, reportedly, a romantic past that’s just now beginning to surface.

His Alleged Ex Comes Forward — and So Do the Photos

Years before Barron graduated from high school and stepped into college life, a surprising voice from his past emerged online. A TikTok user named Maddie, known by her handle @maddatitude, claimed to be his former girlfriend — and brought proof to back it up.

It was revealed that Maddie and Barron had once attended Columbia Grammar and Preparatory School together, a private institution on New York’s Upper West Side.

However, in a 2020 TikTok video, she alleged that they were more than just classmates. “I went to school with Barron Trump, and he was my first ‘bf,'” text in the video read.

The clip then showed two photos, including one where a younger Maddie and Barron appeared side by side in what looked like a school group photo.

She also shared an image of herself and other students posing with Donald and Melania during a class visit to the White House — an event she said took place after the current president’s election victory.

“We gotta save my bae!” she joked in the clip. But despite the sweet tone of her recollection, the relationship didn’t last. It was reported that as Barron prepared to spend his high school years in Florida, the distance proved to be too much.

The young woman has since appeared in other videos online. In 2021, she shared a short TikTok using a filter that showed her as a Barbie doll. “idk who that is but y’all rockin with barbie⁉️,” the caption read.

That same month, Maddie shared another TikTok video lip-syncing to a viral sound and smiling into the camera while appearing to be in a car. She wore her hair in loose waves and completed her outfit with a rose gold chain.

In September of that same year, the blonde beauty, now with visibly darker locks, posted a light-hearted clip enthusiastically dancing to a TikTok song.

To celebrate Halloween, Barron’s allegedly ex-girlfriend shared a glimpse of her costume in a video while lip-syncing to an audio. “#halloween,” the simple caption read. She wore minimal makeup as her loose curls rested on her shoulders.

In July 2023, Barron’s reported ex took to TikTok yet again to share a clip of herself mouthing the words to Drake’s “Pain 1993” featuring Playboi Carti and wowing in a colorful number. “frecks are frecking,” she captioned the post.

In one of Maddie’s more recent social media posts, she showed off her moves as she danced away to Charli XCX’s hit “Apple.” The simple caption read, “ok draft.”

While Barron Trump has kept much of his personal life out of view, glimpses like these offer a rare look at his private world. From a quiet, guarded high school experience to a more social college chapter — and a reported former flame stepping forward — the once-elusive youngest Trump has come into focus.