Barron Trump's Best Friend Is Clearly Crushing On Karoline Leavitt

Bo Loudon, Barron Trump's bestie, has been an influential figure since Donald Trump's 2024 campaign. While Barron clearly wasn't staying on the sidelines, particularly when it came to matching Donald with podcasters, Loudon was often the more public face of their efforts. Post-election, Loudon expanded his fandom to Karoline Leavitt, with a celebratory post on X, formerly Twitter, after she became White House press secretary. Since then, Loudon's gushy posts demonstrate he's swooning over Leavitt.

"Just bumped into my talented and incredible friend Karoline Leavitt at President Trump's Mar-a-Lago club," Loudon declared on TikTok in February 2025, along with a photo of him and Leavitt, each with an arm around the other. In April 2025, Loudon posted a similar pic, touting their shared youth on X. "It's such an honor to be the youngest person to ask @KarolineLeavitt, the youngest Press Secretary in history, a question," Loudon announced. Like Barron, Loudon is 18, nine years younger than 27-year-old Leavitt. That age difference seems minuscule compared to the 30-year age gap between Leavitt and her husband, Nicholas Roccio.

Loudon posted a video of the event on Instagram, where he piled on the praise. The situation resembled an embarrassing middle school exchange as Leavitt called on Loudon, and he tripped over his tongue as he greeted her. Loudon kept his eyes mostly on his notes, looking up occasionally, as he informed Leavitt that she was "wildly popular ... and definitely an inspiration to Gen Z."

As Karoline Leavitt answered Bo Loudon at her White House event, the awkward atmosphere continued. She also referenced her age, laughing uncomfortably after calling herself a "'zillennial,' because I'm right on the cusp of millennial and Gen Z."

In the event photo Loudon posted on his X account, Loudon was roasted for his fashion choices, which created another area of common ground between him and Leavitt. While Leavitt is most often criticized for dressing way older, for the April 30 event, she left the boxy, overly embellished cardigans at home. Instead, she played it safe with a black pleated dress, nude pumps, and an understated cross necklace (rather than her pricey, blinged-out diamond version). Loudon also wore a necklace, and he made the questionable choice of leaving several buttons on his dress shirt undone so he could show off his jewelry. "Put on some socks and button up the shirt you look like a slob," admonished one poster.

This user wasn't the only person who took issue with Loudon putting his bare feet into his loafers. Besides socks looking more polished for a formal occasion, there's an ick factor. "When you're wearing them without socks, you're sweating directly into the shoe, leaving a whole lot of bacteria, and really the shoes start to decay," the YouTube account Real Men Real Style explained. Even if Loudon's not concerned about protecting his footwear investment, any potentially stinky smells are definitely not the way to impress Leavitt.