Donald Trump’s fourth child, Tiffany Trump, has just become a mother for the first time ever. However, while her own family, including her siblings and father, was late to the party, guess who arrived before everyone? Yes, it’s none other than Kimberly Guilfoyle, who could have been Tiffany’s sister-in-law. Kimberly is the ex-fiancée of Tiffany’s brother, Donald Trump Jr.
On May 15, 2025, Tiffany welcomed her first child at around 4:44 am local time. Last fall, it was her father, Donald Trump, who first shared the news of her pregnancy. After giving birth to little Alexander Trump Boulos, Tiffany announced on Instagram.
She shared a photo featuring her hand holding her kid’s tiny foot. Marla Maples, her mom, now proudly Grand Mar Mar, was the first from the Trump clan to congratulate her with a sweet comment, “You rocked it, my girl!”
But surprisingly, the second to arrive was Kimberly Guilfoyle. She not only responded to the announcement but also reposted Tiffany’s Instagram post on her story. “Congratulations @TiffanyTrump and @MichaelBoulos!! Welcome to the world Alexander!” she wrote.
It could have been a heart-touching gesture, but it looked rather like desperation because Guilfoyle was surprisingly one of the first from Tiffany’s circle to congratulate her, even until the mid-afternoon, there were no official congratulations from her siblings Don Jr., Ivanka, or Eric.
Even Trump couldn’t send her a public message, well maybe because her is touring Qatar currently. Rest assured, once he gets free to come back to social media, the Republican leader would make a grand gesture about it.
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The comment from Kimberly was so fast that people doubt whether she was checking Tiffany’s feed all morning, and as soon as the announcement came, she just jumped in. Fans believe that this could be her most cringey move ever to desperately present herself as still a Trump clan member.
More often than not, it’s a great thing when exes remain cordial even after parting ways. But it becomes a complicated situation when only one partner seems to be stuck in one place. Don Jr. has been linked to socialite Bettina Anderson since 2024. Meanwhile, Guilfoyle doesn’t seem to be handling her split from him that well.
According to reports, the former Fox News host was taken aback when their long-time engagement abruptly ended. The real blow came as Don Jr. replaced her very quickly with Anderson. Many sources claim that the new ambassador of Greece might be keeping a close eye on her ex and his new girl.
Her reaction to Tiffany Trump’s announcement just further shows that Kimberly is not willing to let go of it just yet. Yes, she does have a good relationship with the Trump family member, but they are not exactly besties. After all, she wasn’t even invited to Tiffany’s baby shower, while Don Jr.’s new girl, Anderson, smilingly posed with others at the event.
People wonder whether Kimberly was trying to show her loyalty by putting too much effort, or whether she just came across the post and thought to add a comment.
Scroll down for some old images of Kimberly Guilfoyle with Trump siblings
Kimberly Attended the 2019 New York Fashion Week with Tiffany Trump and Marla Maples.
Guilfoyle first crossed path with Don Jr. in 2018 and they were together till 2024.
