Introduction

Karoline Leavitt, at just 27 years old, made history in January 2025 as the youngest White House press secretary under President Donald Trump’s second administration. Her rapid rise in the political sphere has drawn significant attention, but it’s her personal life—specifically her marriage to Nicholas Riccio, a 59-year-old real estate developer—that has sparked widespread curiosity and debate. The couple’s 32-year age gap has raised eyebrows, fueled online speculation, and prompted both admiration and criticism. From their whirlwind romance to their differing approaches to public life, here are the strange and fascinating aspects of Karoline Leavitt’s age-gap relationship with Nicholas Riccio, as revealed through recent media coverage and public discourse.

A Chance Meeting on the Campaign Trail

Leavitt and Riccio’s love story began in 2022 during her congressional campaign in New Hampshire’s First Congressional District. As Leavitt recounted on The Megyn Kelly Show in February 2025, the couple met through a mutual friend at a political event hosted at a restaurant owned by Riccio in New Hampshire. “I was speaking. We met and we were acquainted as friends. And then we fell in love,” she explained. While Leavitt lost her bid against Democratic incumbent Chris Pappas, the campaign introduced her to her future husband, marking the start of an unconventional romance.

What makes this meeting intriguing is the context: Leavitt was a 24-year-old political newcomer, while Riccio, then around 56, was an established businessman with decades of experience. The significant age difference—Riccio was 32 when Leavitt was born—has led some to question the dynamics of their initial connection, especially given the professional setting of a political campaign.

A Rapid Romance and Private Wedding

The timeline of Leavitt and Riccio’s relationship is notably swift. They became engaged over the Christmas holiday in 2023, with Leavitt sharing a photo of Riccio proposing on one knee, captioned, “I get to marry the man of my dreams. I feel SO overwhelmingly BLESSED.” By July 2024, the couple welcomed their son, Nicholas Robert Riccio, nicknamed Niko. Just six months later, in January 2025, they tied the knot in a private ceremony at the Wentworth By the Sea Country Club in Rye, New Hampshire, days before Trump’s second inauguration.

The speed of their relationship—meeting in 2022, engaged in 2023, parents in 2024, and married in 2025—has been described as a “whirlwind romance.” Critics have pointed out that Leavitt was pregnant before their engagement, which some online commentators have labeled a “shotgun wedding,” particularly in light of her public advocacy for traditional Christian values. One Facebook user remarked, “Karoline Leavitt — pregnant before marriage, engaged in December 2023, had a baby in July 2024, and married a rich man 30+ years older than her. Constantly lectures the country about Christian values and the dangers of immorality.” This juxtaposition of her personal choices and public persona has fueled speculation about the authenticity of their relationship.

The Age Gap: A Source of Public Fascination

The most talked-about aspect of Leavitt and Riccio’s marriage is their 32-year age gap. Riccio, born around 1965, was already an adult when Leavitt was born in 1997. A 2005 Sunday Herald article estimated Riccio’s age at 40, placing him at 59 in 2025, while Leavitt remains 27. This significant generational difference has drawn comparisons to other high-profile age-gap relationships, such as Donald and Melania Trump, who share a 24-year age gap.

Leavitt has openly acknowledged the “atypical” nature of their relationship. During her Megyn Kelly Show appearance, when asked if the age gap initially gave her pause, she admitted, “Yes, of course.” However, she emphasized Riccio’s supportive nature, stating, “He’s incredible. He is my greatest supporter, he’s my best friend, he’s my rock.” She also noted that Riccio’s established career allows him to support her demanding role as press secretary, saying, “He’s built a very successful business himself so now he’s fully supportive of me building my success in my career.”

Despite Leavitt’s positive portrayal, the age gap has sparked harsh criticism online. Social media platforms, particularly X, have been rife with comments mocking the couple. One user wrote, “Karoline Leavitt’s husband was 33 when she was born… I see why she works for a felon, rapist, and accused pedophile now.” Another commented, “The tradition of bringing your dad and baby to the… oh wait, that’s your husband,” in response to a family photo Leavitt shared at the White House Easter Egg Roll. These remarks highlight the public’s fixation on the age difference and the sometimes cruel tone of the discourse surrounding it.

Contrasting Personalities and Social Media Presence

Another peculiar aspect of Leavitt and Riccio’s relationship is their starkly different approaches to public life. Leavitt, a seasoned communicator and political figure, is active on social media, frequently sharing updates about her career and family. Riccio, however, is notably private, with no social media presence. Leavitt addressed this in a now-deleted Instagram post, stating, “He doesn’t have social media and he’s an introvert (complete opposite of me). I respect his privacy on here — but he’s my number one fan, the best dad, and just the best man I’ve ever met.”

This contrast has raised questions about potential tensions in their relationship. Relationship expert Janet Bayramyan, speaking to Women.com, noted that differing approaches to social media can lead to issues if one partner feels their boundaries are not respected. For instance, Leavitt’s occasional posts about Riccio, such as their engagement or family photos, have drawn negative comments, which may conflict with his preference for privacy. Despite this, Leavitt insists that their differences complement each other, describing Riccio as a supportive partner who balances her outgoing personality.

Riccio’s Background and Supportive Role

Nicholas Riccio’s backstory adds another layer of intrigue to the couple’s dynamic. A self-made real estate developer, Riccio overcame significant hardships, including homelessness at 18, to build Riccio Enterprises LLC, a multimillion-dollar property business in New England. His success in real estate, particularly in transforming properties in areas like Hampton Beach, has made him a prominent figure in New Hampshire’s business community. A 2005 Portsmouth Herald article highlighted his ambition to own a professional sports team, though there’s no evidence he achieved this goal.

Riccio’s financial stability and flexibility have allowed him to support Leavitt’s high-profile career. After giving birth to their son Niko on July 10, 2024, Leavitt returned to work just four days later, motivated by an assassination attempt on Trump on July 13. She told The Conservateur, “I looked at my husband and said, ‘Looks like I’m going back to work.’” Riccio’s ability to travel with their son and manage family responsibilities has been crucial, but some critics argue that his career may have taken a backseat to Leavitt’s, potentially creating an imbalance.

Public Scrutiny and Cultural Context

The public’s fascination with Leavitt and Riccio’s age gap reflects broader cultural attitudes toward May-December romances. While age-gap relationships are not uncommon—celebrity examples include George and Amal Clooney (17 years) and Priyanka Chopra and Nick Jonas (10 years, with Jonas being younger)—they often face scrutiny, particularly when the man is significantly older. Leavitt’s role as a conservative figure defending “traditional values” has intensified this scrutiny, as critics highlight the perceived contradiction between her public stance and her personal life.

Dating expert Anthony Recenello, speaking to The List, argued that age gaps are not inherently problematic as long as couples communicate effectively and share mutual respect. “The age difference can highlight mismatches faster, but it doesn’t cause them,” he said, noting that Leavitt’s emotional intelligence likely helps navigate their dynamic. Nonetheless, online critics continue to speculate about power imbalances, with some suggesting Riccio’s wealth influenced Leavitt’s decision to marry him.

Conclusion

Karoline Leavitt and Nicholas Riccio’s 32-year age-gap romance is a complex and compelling story that defies simple categorization. From their serendipitous meeting during a political campaign to their rapid progression to marriage and parenthood, their relationship has captured public attention for its unconventional nature. While Leavitt portrays Riccio as her greatest supporter and a devoted father, the significant age difference, combined with their contrasting personalities and the public’s harsh commentary, raises questions about the dynamics of their marriage. As Leavitt navigates her historic role as White House press secretary, her personal life remains a topic of fascination, reflecting broader societal debates about love, age, and power. Whether their “atypical love story” endures the scrutiny remains to be seen, but for now, Leavitt and Riccio appear committed to making it work, proving that love can indeed transcend age—though not without its challenges.