Kimberly Guilfoyle's Brother Has A Massive Age Gap With His Wife

When it comes to relationships in the public eye, age gaps often spark curiosity. Kimberly Guilfoyle and Donald Trump Jr. had a noticeable age gap of eight years before they called off their engagement in 2024. But while this gap may not sound too drastic, Kimberly's brother is in a relationship with an eyebrow-raising age difference.

At 53, Anthony "Tony" Guilfoyle Jr. married Republican business owner Lyda Loudon, 29, in a glamorous event in Ireland, making their age gap a whopping 24 years. The wedding took place in a medieval castle in March, 2025, and featured a guest list of high-profile Republicans and Trump supporters, including Lyda's mother and media personality Dr. Gina Loudon, and the bride's father, a former member of the Missouri senate — both of whom are only a few years older than their new son-in-law. This was all too apparent in photos of Tony walking his mother-in-law down the aisle before the wedding ceremony as the pair looked like they themselves could be a couple.

The groom's sister also took center stage walking down the aisle as a maid of honor. Even though Kimberly Guilfoyle was grieving the loss of her ex-fiancé to girlfriend, Bettina Anderson, she was reportedly in high spirits for her brother's nuptials. "Kimberly was beaming the whole day," an insider revealed (via the Daily Mail). "She was dancing, socializing, singing away with friends, loving every part of it ... Nobody was happier than her."

While Kimberly Guilfoyle was clinging to the last remnants of her and Donald Trump Jr.'s romance, her younger brother Anthony "Tony" Guilfoyle was taking his relationship to the next level at his and Lyda Loudon's lavish 2025 wedding. Lyda, who runs her own marketing company, met Tony, an energy drink executive, in 2023 in Palm Beach, Florida, and got married two years later. The pair also share a Shih Tzu, Charli, who was trained to be the ring bearer at the wedding.

Even though Tony has close ties with the Trump family due to his sister's former dalliance with President Trump's eldest son, Lyda's family are also members of the president's inner circle and frequent visitors of Mar-a-Lago. The Loudon family have been vocal in their support of the Trump campaign and administration, with the matriarch, Dr. Gina Loudon, holding roles as co-chair of Women for Trump 2020 and senior anchor at America's Voice News where she pushes Trump-centered media. Furthermore, Lyda's brother and conservative social media influencer, Bo Loudon, has been friends with Barron Trump since childhood.