Barron Trump's Pal Can't Hide His Cheeky Behavior Around Karoline Leavitt (Nicholas Riccio WYA)

We all know by now that Karoline Leavitt has an awkward age gap in her marriage. Yet, while Leavitt's husband, Nicholas Riccio, is 32 years her senior, she may have just caught the eye of a much younger man. And, that younger man might be the pal of her boss' son. On April 30, Barron Trump's self-proclaimed "best friend" Bo Loudon joined in on Leavitt's briefing for influencers. And, he seemed to get a bit tongue-tied.

When Leavitt called on Loudon, he began by saying, "H-hi, Karoline ... So, um ..." per Instagram. Loudon certainly sounded nervous, and this could have simply been a result of having all eyes on him. Yet, the question he asked was focused on Leavitt. "As the youngest press secretary in history, who is a wife and a mom, you've become wildly popular with 'America First' patriots. Um — as an 18-year-old, I can say you're definitely an inspiration to Gen-Z. Uh — what has been the biggest highlight for you in these first hundred historic days?" In these particularly curated press briefings, almost all of the questions put a pointedly positive spin on Donald Trump and his administration. So, the sycophancy of Loudon's question certainly isn't out of the ordinary. It is, however, interesting that Loudon chose to focus his question on Leavitt, specifically.

In Karoline Leavitt's answer to Bo Loudon's flattering question, she noted that, like Loudon, she is a member of Gen-Z. At 27 years old, Leavitt is nearly a decade older than Loudon. Yet, the two are much closer in age than Leavitt and her husband are. Age seems to be something that Leavitt might have some insecurities about. Leavitt often seems to be trying to bridge her age gap with Riccio by wearing stuffy old lady outfits that make her appear more mature. So, if Leavitt gets the feeling that Loudon is crushing on her, she'll probably nip that in the bud before anyone realizes that she's much closer in age to his BFF Barron Trump than she is to Donald Trump.

Regardless of whether Loudon has a crush on Leavitt or just had a case of stage fright, he made it clear that he's a fan of the press secretary. He posted a photo of the two posing together on X, formerly known as Twitter and wrote, "It's such an honor to be the youngest person to ask @KarolineLeavitt, the youngest Press Secretary in history, a question as part of the New Media Briefings. God bless President Trump, Karoline Leavitt, and this incredible administration!" So, we have a feeling that Loudon will be getting called on in another press briefing soon enough.