Barron Trump's Family Just Can't Stay Quiet About His Dating Life

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Once Barron Trump turned 18 years old and started attending college, the prospects of his dating life began being discussed, not only by media outlets but by other members of the Trump family. While campaigning for the 2024 presidential election, Donald Trump made the rounds on several high-profile podcasts, which included an October 17 stop on the "BPD Podcast" hosted by Patrick Bet-David. During the sit-down, Donald showed he had a strange relationship with Barron by airing details of his son's dating life, or lack thereof. Bet-David asked if Barron had a special lady in his life, and Donald blurted out a response. "I'm not sure he's there yet," he told the podcast host. "I don't think he's had a girlfriend yet." Donald also said of his son's social life, "He doesn't mind being alone, but he's somebody that gets along with people." Not only did his dad blow up his spot, but shortly after that interview, one of Barron's brothers weighed in on his dating life.

While speaking to the Daily Mail on October 29, Eric Trump was asked about Barron's future, and he took an odd approach to discussing his much-younger brother. "My advice to Barron is you are the most watched person, probably the most watched bachelor in the world right now," Eric said, adding that he did not experience the same scrutiny as Barron at that age. "Just be careful, just be careful. There are a lot of eyes on you," he warned the teen.

Not only did Barron's dad and brother have thoughts to share about his romantic life, but so did fellow students at New York University. One classmate told the Daily Mail in September that Barron would "become kind of liberal" if he started dating at NYU. However, dating at college could prove to be challenging for Barron with his mother in tow.

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When Barron Trump was still scouting which college he would be attending, a source confirmed that Melania Trump would be staying close to her son. "Melania's main job is taking care of Barron, and I think it's possible that she will follow him wherever he goes to school," the insider told People in March, when the teenager was still finishing up his senior year of high school. Of course, he wound up choosing New York University, which allowed Barron to resume a familiar living situation: residing in Trump Tower with his mom. Living with Melania could cause difficulties for Barron's love life, especially considering what type of mother she has reportedly been to her only child. "She is a doting mother to Barron and very protective of him. This is nothing new," a separate source told People for an article published in March 2023.

Prior to his decision to go to NYU, some wondered if Barron would choose the same school as his rumored ex-girlfriend. An old video from a TikTok user named Maddie, who went by @maddatitude on the app, resurfaced just before Barron started classes, and it shed some light on his dating history. "For those asking ... I went to school with Barron Trump, and he was my first bf," Maddie wrote in a TikTok posted in June 2020. It's believed the pair attended Columbia Grammar and Preparatory School in New York City's Upper West Side together. Maddie's video about her supposed ex-bae went viral, and she spoke about their relationship in the comment section, describing Barron as a "lil shy boy." The TikToker also gave a classic excuse as to why she and Barron broke up. "[H]e went to Florida for the summer so we ended it," Maddie wrote, replying to another user.