Kimberly Guilfoyle's Brother and His Spouse Have a Significant Age Difference that Makes Others Uncomfortable

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Kimberly Guilfoyle looks serious during speech

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Kimberly Guilfoyle is no stranger to rumors and controversies, but it turns out she isn’t the only Guilfoyle with a shady side. The younger brother of the U.S. ambassador to Greece made headlines in March when he joined Donald Trump’s inner circle by marrying the daughter of Gina Loudon, a member of his presidential campaign’s media advisory board during his 2020 run. The scandalous part? Tony Guilfoyle is around his mother-in-law’s age. It must be a family thing.

His sister’s partners have also been getting younger with time. Kimberly and ex-fiancé Donald Trump Jr. had a nine-year age gap. Kimberly’s ex-husband, Eric Villency, was also her junior, but not by as much. Born in June 1975, the furniture heir is six years younger than Kimberly, born in March 1969. This trend wasn’t always there, though. She was actually a year and a half younger than her first husband, California Governor Gavin Newsom, though the age similarity hasn’t prevented Kimberly and Newsom from not standing each other.

Their preference for younger partners isn’t the only thing Kimberly and Tony bond over. The two have been close since they were kids. She has always felt protective of her brother, especially since taking on a maternal role in his life after their mother died of leukemia when she was 10 and he was 8. In 2017, she made her love for him public. “So blessed to have you in my life,” she wrote on Facebook. Kimberly and Tony have indeed plenty in common.

Tony Guilfoyle is more than two decades older than Lyda Loudon

On March 29, Kimberly Guilfoyle welcomed a sister-in-law into her life, albeit one who is closer in age to her son than herself. At 53, Tony Guilfoyle wed 29-year-old Lyda Loudon, seen above between Gina Loudon and Kimberly. Kimberly was the maid of honor in the wedding celebrated at Ashford Castle in Ireland, their late father’s homeland. Despite the high profile of the people they’re associated with, Tony and Lyda wanted to keep the wedding away from the spotlight.

That’s not to say the festivities were low profile. “They wanted their wedding to be an incredible spectacle for their closest family and friends. It was all of that and more,” a source told the Daily Mail. Also present was Lyda’s father, John William Loudon, a former Missouri state senator who is only four years older than his son-in-law, and her siblings. Her youngest brother, Bo Loudon, is actually Barron Trump’s self-proclaimed best friend.

According to the Daily Mail, Tony and Lyda had been dating for two years after meeting in Palm Beach. The couple made the big day even more special by making their shih tzu, Charli, their ring bearer. “This still makes me cry and I didn’t even cry at the wedding very much! But something about how you present it from Charli’s view is so sweet and touching!” Gina commented on an Instagram video shared by Wedding Dog Sitter, the company that helped with Charli’s wedding role.