Kimberly Guilfoyle’s Cryptic Valentine’s Post Sparks Speculation Amid Don Jr.’s New Romance

Kimberly Guilfoyle appears to be sending a subtle message to her former fiancé, Donald Trump Jr., and his new girlfriend, socialite Bettina Anderson, as the couple prepares to celebrate their first Valentine’s Day together. Days after Anderson flaunted her lavish Valentine’s Day gift basket on social media, Guilfoyle shared a cryptic post featuring a bouquet of pink roses—a classic romantic gesture—on her Instagram Story.

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The flowers, sourced from Miami’s luxury florist Le Boutique Royal and valued at approximately $250, were posted with a simple caption: “Thank you” accompanied by two pink heart emojis. The lack of a named sender sparked speculation that the former Fox News host might have a new suitor.

Guilfoyle and Trump Jr. ended their relationship a few months ago, and while he has since moved on publicly with Anderson, the two exes have maintained a cordial relationship. They were recently spotted together at The Club at Admirals Cove’s annual street fair, where two of Trump Jr.’s children were present, according to The List.

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Despite her public show of moving on, insiders claim Guilfoyle is still coming to terms with Trump Jr.’s new romance. A source told People that at President Trump’s inauguration, she kept a “watchful eye” on Anderson and her former fiancé. “Kim is still very fond of Don and was paying attention,” the source said.

“She knows how beautiful and well-dressed Bettina is, and there is no question that she was hurt when her romance with Don ended.” Anderson, now the U.S. ambassador to Greece, recently showcased her Valentine’s Day preparations, posting a delivery from luxury food brand Portage Foods featuring premium smoked fish and caviar, per Daily Mail.

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She captioned it, “Ready for Valentine’s Day,” alongside champagne glass emojis and the song Caviar and Champagne playing in the background. Meanwhile, over the weekend, Trump Jr. and Anderson further solidified their relationship by attending the Super Bowl together, accompanied by three of his five children. The couple enjoyed the game from a VIP suite, with Anderson embracing her new role in his life.

Guilfoyle was also at the Super Bowl but was notably absent from Trump Jr.’s circle. Instead, she was seen posing for photos with Yellowstone star Kevin Costner, adding to speculation that she is forging a new path post-breakup. As Valentine’s Day approaches, it seems both Trump Jr. and Guilfoyle are making statements—one with a new romance, the other with an air of mystery surrounding her next chapter.