Karoline Leavitt, 27, made history by becoming the youngest White House press secretary in January 2025, but her age continues to make headlines for all the wrong reasons.
The official spokesperson for President Donald Trump’s second administration is married to real estate developer Nicholas Riccio, a man who is more than 32 years Leavitt’s senior.
In January 2025, Leavitt and Riccio tied the knot at New Hampshire’s Wentworth By The Sea Country Club. The wedding ceremony took place days before Trump was inaugurated for his second term.
Riccio is 60 years old. The three-decade age gap between the former Plymouth State University student and the mother of his infant son remains a topic of conversation.
Leavitt and Riccio are not the only high-profile couple who face constant questions about a significant age difference. Ex-NFL coach Bill Belichick’s relationship with a former college cheerleader remains a trending topic, too.
Belichick, 73, dated 61-year-old Bill Belichick Foundation executive director Linda Holliday for 16 years from 2007 to 2023, until he got romantically involved with 24-year-old Jordon Hudson in 2023.
Since stepping out together, Belichick and Hudson have become targets of digs at the hands of celebrities like retired Patriots player Rob “Gronk” Gronkowski and hip-hop legend Snoop Dogg.
Leavitt’s marriage to Riccio has been the regular butt of jokes, too. The May 22 episode of the Fox News show “Jesse Watters Primetime” featured comedian Matt Friend, 26, clowning Leavitt by offering her a specific warning on the conservative network.
“By the way, Karoline Leavitt, stay away from Bill Belichick! Stay away from Bill Belichick! She likes a big-ole’ man, Jesse. She really does,” Friend jokingly said in a video that has been shared on X.
A laughing Watters quickly tried to cut to a commercial break. The 16-second clip sparked reactions online as X users shared their thoughts on Friend comparing Leavitt and Riccio to Belichick and Hudson.
“Karoline is too old for Belichick,” read one response on the social networking app. A second person stated, “She already has her own ‘Belichick.’”
A third individual tweeted, “Good advice. Karoline, some things are better left untouched, especially Bill Belichick’s playbook.” A fourth noted, “What an absolute unhinged thing to say on the air.”
Friend uploaded the full “Jesse Watters Primetime” segment to his YouTube channel, where he did impressions of Trump, Vermont Sen. Bernie Sanders, Minnesota Gov. Tim Walz, and cable television host Bill Maher.
The social media personality’s takedowns targeted both sides of the aisle. He also made fun of Watters, Tesla CEO Elon Musk, Secretary of Defense Pete Hegseth, former President Joe Biden, and the Democratic Party.
“Love how Jesse was so irritated by this and wanted to cut this short, and love how Matt gives it to these idiots right on their home turf,” read a comment under Friend’s YouTube video.
Another viewer wrote, “You can tell that Jesse is forcing himself to smile and laugh. He is incapable of sincerity on any level. You can tell he is pretty ticked off, though!”
“His jokes aren’t funny, but his impressions are hilarious,” read a balanced critique of Friend’s comedy, while a harsher critic declared, “Weak imitations on this video… He’s off his normal game.”
Friend began his career in show business as a production intern for “The Tonight Show Starring Jimmy Fallon.” The graduate of New York University’s Gallatin School eventually performed at the 2024 White House Correspondents’ Association Dinner during the Biden administration.
As for Leavitt, the unsuccessful 2022 Republican congressional candidate addressed marrying an older man while speaking with Fox News alumna Megan Kelly. The interview took place on the right-wing pundit’s self-titled digital show.
“I met my husband during my congressional campaign. A mutual friend of ours hosted an event at a restaurant that he owns up in New Hampshire and invited my husband,” Leavitt told Kelly in February 2025.
She continued, “Of course. It’s a very atypical love story, but he’s incredible. He is my greatest supporter. He’s my best friend. He’s my rock.”
Leavitt and Riccio are parents to a son named Nicholas Robert Riccio. The baby, also known as Niko, was born on July 10, 2024.
