Comedian Matt Friend popped onto Fox News to sit down with personality Jesse Watters to combine some roasting with some impressions, according to his own Instagram post. However, the camaraderie veered toward the absurd when Friend clearly made Watters uncomfortable with a throwaway joke at the expense of White House Press Secretary Karoline Leavitt and her much older husband Nicholas Riccio. As he was signing off, Friend tossed out, “By the way, Karoline Leavitt, stay away from Bill Belichick.” To which Watters quickly said, “We’ve gotta go.”

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Friend: By the way, Karoline Leavitt, stay away from Bill Belichick.

Watters: We’ve gotta go pic.twitter.com/7pyegnzfxR

— Acyn (@Acyn) May 23, 2025

What Friend was slyly poking at was the rather aggressive age gap relationship between Belichick and girlfriend Jordon Hudson and how this mirrors the marriage Leavitt finds herself in. Of course, every time Leavitt tries to show off her older husband, she gets roasted for it, which most likely gave Friend the courage to make such a joke on air. While Leavitt often wears outdated clothing, possibly in an attempt to distract from how much younger she is than Riccio, it might not be enough to convince the masses that her relationship is not a joke.

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