How Donald Trump Jr.'s Siblings Really Feel About Kimberly Guilfoyle

Donald Trump Jr. and Kimberly Guilfoyle got engaged on December 31, 2020 after dating since 2018. The couple had known each other for years before they dated, and Guilfoyle had spent a lot of time with her fiancee's siblings prior to their engagement. Eric Trump, Tiffany Trump, and Ivanka Trump formed varying levels of bonds with their brother's future wife. There had even been evidence of friction between Guilfoyle and Trump family members.

Both Eric and Tiffany seemed to forge close relationships with Guilfoyle. In February 2019, Tiffany attended New York Fashion Week along with her mother, Marla Maples. She also brought Donald Jr.'s then-girlfriend along for the evening. The following year, Eric gushed over his brother's bride-to-be at her birthday party in March 2020. "You're so freaking beautiful I might take you home tonight," Eric joked while giving a speech, per the Daily Mail. Ivanka also grabbed the mic at the birthday party, but was far less effusive. "The second best thing to a really funny speech is a short speech so I'll keep it at that," she said while mentioning Guilfoyle's contributions to her father's political campaign.

The following year, in April 2021, Guilfoyle and Donald Jr. celebrated a friend's wedding in Key Largo with Eric and his wife Lara Trump, along with Tiffany and her future husband, Michael Boulos. Later, it was at Tiffany's wedding where tension between Guilfoyle and Ivanka started to show.

When Tiffany Trump married Michael Boulos in November 2022, Ivanka Trump posted a carousel of pics to Instagram along with a gushing caption. "When I was 12 years old my dream of having a baby sister came true!" Ivanka wrote in the opening of the caption. Among her snaps was a photo of the Trump ladies which included Ivanka, Tiffany, Lara Trump, Melania Trump, and Marla Maples (Tiffany's mom). Later, it was revealed that she had stealthily cropped Kimberly Guilfoyle from the group photo.

According to a source at the Daily Mail, Ivanka leaving out Donald Trump Jr.'s long-time partner was simply an oversight, as she eventually posted the original photo to her Instagram Stories. "Ivanka loves Kimberly and in no way would crop her out," the insider told the outlet in November 2022. "The two women are very close and Kimberly has really become part of the Trump family," they added. Following the cropping fiasco, rumors started to circulate that members of the Trump family were not keen on Don Jr's future wife. Meanwhile, Eric Trump — who had a close relationship with Guilfoyle — refuted those claims. "I completely disagree with the narrative and happen to think the world of Kimberly," Eric told Page Six in December 2022.

Reportedly, Guilfoyle's choice to wear a black dress, while everyone else wore pastel colors, at Tiffany's wedding was the reason for the snub. More evidence would later surface that Ivanka was not fond of Donald Jr.'s fiancee.

A few months after Ivanka Trump cropped Kimberly Guilfoyle out of the photo from Tiffany Trump's wedding, a report claimed that the cropping was indeed intentional. "Ivanka doesn't trust [Guilfoyle] because she sees her as a social climber desperate to marry into the family," a source told OK! in February 2023, while adding that Guilfoyle's choice of a black dress "upset both Tiffany and Ivanka."

Not long after that report surfaced, Donald Trump Jr. threw a birthday party for his bride-to-be in March 2023. Eric Trump was in attendance along with his wife Lara Trump, but Ivanka and husband, Jared Kushner were noticeably absent. "They were invited to Kimberly's birthday party and were so sad to miss it," a source told Page Six at the time. "Their niece's bat mitzvah was Thursday evening and it had been planned a long time ago." That seemed a valid reason to miss the birthday bash, but Ivanka and her husband used a similar excuse when they missed a party thrown by Donald Jr. and Guilfoyle at their mansion months earlier in December 2022.

When Tiffany celebrated her one-year wedding anniversary in November 2023, she took to Instagram to commemorate the occasion. Guilfoyle popped up in the replies. "Happy anniversary sweethearts we love you!" she commented on the post. What makes that notable is that Tiffany neglected to like or reply to her future sister-in-law's comment. Perhaps it was just an oversight, similar to when Ivanka cropped Guilfoyle out of the wedding picture.