Inside The Kimberly Guilfoyle And Anthony Scaramucci Affair Rumors

Before Kimberly Guilfoyle began her relationship with Donald Trump Jr., she was rumored to have had an affair with well-known figure in Republican politics, Anthony Scaramucci. It appears that whispers about the two began in July 2017 when reporter Olivia Nuzzi tweeted that Guilfoyle had joined Scaramucci, Donald Trump, and Melania Trump for dinner. This allegedly infuriated Scaramucci, who believed it would raise suspicions about his dealings with Guilfoyle. Shortly after this outing, the Wall Street financier's wife, Deidre Ball, filed for divorce.

While the dinner was made public, Guilfoyle and Scaramucci may have been getting close a month before. Showbiz 411 claimed the pair were spotted apartment hunting in June 2017.  However, one insider dismissed these claims to People, divulging in August 2017 that, "They share the same real estate agent in New York and she lives in The Beresford and he was looking in The Beresford." Even Trump's former close friend Roger Stone shot down the rumors, telling the HuffPost, "He is way too short for Kimberly." Still, their denial did not quiet the chatter surrounding their relationship, especially after they were spotted out of the country together.

Kimberly Guilfoyle and Anthony Scaramucci cozied up during a September 2017 outing in Rome. The former Fox News correspondent and Scaramucci were photographed at the Celebrity Fight Night event. It's unknown if they arrived in Rome together or were both invited to the function.

The following month, insiders told Page Six that the ousted White House staffer was indeed getting close to Guilfoyle, but they were taking their time. "Kimberly thinks the world of Anthony. He is one of her best friends, but they are not a yet a couple. He is still going through a divorce. She is a single mom, and her son is her priority," the source stated in October 2017. However, once November 2017 rolled around, if there was anything romantic going on, it seemed to have fizzled out, as Scaramucci and wife, Deidre Ball, reconciled. Still, the friendship seemed to remain intact, as the two were seen together once again just months later.

In an effort to repair their marriage, Anthony Scaramucci and Deidre Ball even appeared in a March 2018 episode of "Dr. Phil." Ball told the TV host, "I just wanted my family back and I loved him and I wanted my kids to have their dad and we're working on it and it's how it should be" (via Page Six). It's unclear how she feels about her husband's friend and their alleged affair. Still, Scaramucci remained on speaking terms with Kimberly Guilfoyle.

During the same month that the "Dr. Phil" episode aired, the pals reunited in what appeared to a serious meeting. Someone who witnessed the moment told Page Six that Scaramucci and Guilfoyle seemed tense in their chat, though the context is unknown. "They were standing inches apart and they were keeping their voices low," the individual stated, adding, "The conversation looked serious." It's also unclear where this meeting took place or if anyone else was present. Guilfoyle has moved on with Donald Trump Jr., whom she got engaged to in December 2020, seemingly leaving any potential romance with Scaramucci behind.