Kimberly Guilfoyle's Congrats On Tiffany Trump's Baby Is Her Cringiest Move Yet The List
Tiffany Trump welcomed her first child, and Donald Trump Jr.'s ex Kimberly Guilfoyle was quick to hop in to congratulate her...ahead of Tiffany's actual family.
By May 15, 2025 5:13 pm EST
There's a new member of the Trump family, and one would-be member is gladly sharing the news. Tiffany Trump, the fourth of the five Trump children, welcomed her first child at 4:44 AM on May 15, 2025. President Donald Trump spilled the beans about Tiffany's pregnancy last fall, but she was the first to announce the arrival of little Alexander Trump Boulos via an Instagram photo featuring her hand holding his tiny foot. Mom Marla Maples (who now holds the proud title of "Gran Mar Mar"), was, of course quick to offer her love and congratulations, saying, "You rocked it, my girl!" But not far behind her was Kimberly Guilfoyle, the ex-fiancĂŠe of Tiffany's brother Donald Trump Jr. Guilfoyle not only responded to the announcement, but she also reposted the photo on her Instagram Stories with another congratulations to the new parents.Â
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A post shared by Tiffany Trump (@tiffanytrump)
The gesture would be sweet if it didn't look so much like desperation. Guilfoyle got in her say long before any of Tiffany's other family members; as of mid-afternoon on the 15th, there was no social media acknowledgment from siblings Don Jr., Eric, or Ivanka. (Youngest brother Barron Trump isn't on social media as of yet.) Grandpa Donald is busy doing business in Qatar, but no doubt he'll get a moment at some point to give his daughter a call. It was almost as if the former Fox News host had been checking Tiffany's feed all morning just so she could beat everyone to the top of the comments list.
It's always admirable when exes remain friendly even after they realize they weren't meant for each other. But when one partner can't seem to move on, then the situation becomes stickier. Insiders have hinted that Kimberly Guilfoyle hasn't been handling her split from Donald Trump Jr. as well as it may seem. They report that the new ambassador to Greece was naturally stung at the sudden end to their long-time engagement, particularly because she was being replaced by socialite Bettina Anderson. Guilfoyle has been spotted keeping a close eye on the new couple during social events, as if wondering what might have been.
The reactions to Tiffany Trump's baby news are another clue that Guilfoyle is finding it hard to let go. Yes, the two may still be on chummy terms, but they're not what you'd call besties. Case in point: Guilfoyle wasn't invited to Tiffany's baby shower (though she would have fit in, since it was a bit of a fashion nightmare). Anderson, on the other hand, was on the guest list, posing happily with the mom-to-be and other family members.Â
Offering congratulations to a might-have-been sister-in-law is a lovely gesture, yet the timing on Guilfoyle's part is just squirmy. Did she just happen to come across the announcement while looking for pro-Trump memes to copy and paste? Or did she realize that no one would be texting her the news, so checking Tiffany's feed would be the only way to find out?Â