From Twitter DM to Family Life: The Enduring Love Story of Kayleigh McEnany and Sean Gilmartin

Kayleigh McEnany, a prominent political commentator and former White House Press Secretary, has maintained a relatively private romantic life, with her enduring partnership with former Major League Baseball pitcher Sean Gilmartin being her sole publicly known significant relationship. Their journey from an unconventional meeting to building a family together exemplifies a steadfast commitment amidst demanding public careers. Their love story, rooted in shared values and mutual support, has unfolded over nearly a decade, culminating in marriage and the raising of their children.

The couple's romance began in 2015 under modern circumstances. McEnany, then a Harvard Law student working a summer job in New York City, discovered Sean Gilmartin's profile on X (formerly Twitter). At the time, Gilmartin was playing for the New York Mets. Intrigued, McEnany took the initiative to contact him through the platform. This initial digital connection quickly blossomed into an in-person meeting, with their first date taking place at a restaurant called Southern Hospitality. They spent that summer together, fostering a deep connection that laid the groundwork for their future.

After that pivotal summer, their relationship continued to develop, despite the geographical challenges posed by their burgeoning careers. McEnany returned to Harvard Law, while Gilmartin continued his professional baseball career, playing for various teams across the country. They navigated a long-distance relationship, a testament to their early commitment to one another. Their dedication culminated in their marriage in November 2017, a significant milestone that solidified their bond.

The early years of their marriage were characterized by continued long-distance living, as McEnany's career in politics took her to Washington D.C., eventually leading to her high-profile role as White House Press Secretary, while Gilmartin's baseball career kept him on the road. Despite the demanding nature of their professions, they prioritized their relationship, finding ways to stay connected and support each other's aspirations. This period underscored the strength of their partnership and their ability to thrive under challenging circumstances.

Their family began to grow with the arrival of their first child, daughter Blake Avery, in November 2019. Blake's birth came during a particularly intense period for McEnany, as she was serving as the national press secretary during the Trump administration. The couple welcomed their second child, son Nash, in November 2022. These additions further cemented their family unit, bringing new joys and responsibilities into their lives.

In March 2025, McEnany publicly announced that she and Gilmartin were expecting their third child, due in June 2025. This news highlighted their continued commitment to expanding their family and building a life together. Their public appearances and social media presence often showcase their close-knit family, reflecting their shared values and dedication to their children. McEnany has frequently spoken about the importance of faith in their marriage and family life, describing it as a foundational element of their bond.

Sean Gilmartin, who retired from professional baseball in 2020, has since transitioned to supporting McEnany in her media career, often appearing alongside her. Their relationship is often portrayed as a strong partnership, balancing the demands of public life with their private family commitments. McEnany frequently expresses gratitude for Gilmartin's unwavering support and their mutual respect, which has allowed them to navigate the complexities of their high-profile lives while maintaining a grounded and loving home. Their story stands as a testament to an enduring partnership, built on a foundation of early connection, sustained through distance, and enriched by their growing family.