Unraveling rumors of Donald Trump Jr's fiancee Kimberly Guilfoyle's affair with Anthony Scaramucci

NEW YORK CITY, NEW YORK: Before Kimberly Guilfoyle's high-profile relationship with Donald Trump Jr, rumors swirled about her alleged affair with another prominent Republican figure, Anthony Scaramucci.

These whispers started circulating in mid-2017, fueled by a series of public sightings and insider reports. Although both parties denied any romantic involvement, their close association continued to draw attention.

Here’s a detailed look into the events and allegations that linked Guilfoyle and Scaramucci.

Rumors begin about an affair between Kimberly Guilfoyle and Anthony Scaramucci

The speculation began in July 2017 when reporter Olivia Nuzzi tweeted that Guilfoyle had joined Scaramucci, Donald Trump, and Melania Trump for dinner. The tweet sparked controversy, as insiders claimed Scaramucci was furious about the public revelation, fearing it would raise suspicions about his dealings with Guilfoyle. 

Shortly after this dinner, Scaramucci’s wife, Deidre Ball, filed for divorce, adding fuel to the fire.

What's more? Reports from Showbiz 411 suggested that Guilfoyle and Scaramucci were seen apartment hunting together in June 2017. However, sources close to them quickly dismissed these claims.

An insider told PEOPLE Magazine in August 2017, "They share the same real estate agent in New York, and she lives in The Beresford and he was looking in The Beresford."

Trump's former close friend Roger Stone also dismissed the rumors, telling HuffPost, "He is way too short for Kimberly." Despite these denials, the speculation persisted, especially after the pair were spotted together outside the country.

Kimberly Guilfoyle and Anthony Scaramucci's close encounter in Rome

In September 2017, the rumors gained more traction when Guilfoyle and Scaramucci were seen together in Rome. They attended the Celebrity Fight Night event, where they were photographed looking cozy.

It remains unclear if they traveled to Rome together or were simply both invited to the function.

The following month, insiders told Page Six that the relationship was blossoming, albeit slowly. "Kimberly thinks the world of Anthony. He is one of her best friends, but they are not yet a couple. He is still going through a divorce. She is a single mom, and her son is her priority," remarked a source in October 2017.

By November 2017, any romantic involvement seemed to have cooled down, as Scaramucci and his wife, Ball, reconciled. However, the friendship between Guilfoyle and Scaramucci appeared to remain intact, as per The List.

In March 2018, Scaramucci and Ball appeared on an episode of 'Dr Phil' to discuss their efforts to repair their marriage.

Ball expressed her desire to restore their family, saying, "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," as quoted by Page Six.

Kimberly Guilfoyle and Anthony Scaramucci's tense reunion

Scaramucci and Guilfoyle were spotted together again in March 2018, and they appeared to be having a serious conversation. An eyewitness told Page Six that the two appeared tense.

"They were standing inches apart and they were keeping their voices low," stated the source, adding, "The conversation looked serious." The context of this meeting remains unclear.

Guilfoyle has since moved on with Don Jr, to whom she got engaged in December 2020. The engagement appears to have put any rumors of a romance with Scaramucci firmly in the past.