Kimberly Guilfoyle isn’t letting her ex-fiancé’s new relationship steal the spotlight this Valentine’s Day.
While Donald Trump Jr. and his new girlfriend, socialite Bettina Anderson, prepare to celebrate their first romantic holiday together, Guilfoyle has shared a glimpse into her own love life—one that seems to be flourishing just fine without him.
A Valentine’s Day Message Without Words
Just days after Anderson flaunted an extravagant gift basket filled with luxury treats for the occasion, Guilfoyle responded in her own way.
She posted a picture featuring a classic Valentine’s Day staple—roses.
The bouquet of bright pink flowers, sourced from Miami’s high-end florist Le Boutique Royal, retails for around $250.
Rather than tagging or mentioning the sender, she simply captioned the post with a coy ‘thank you’ and two pink heart emojis, leaving her followers—and possibly her ex—guessing.
The Subtle Social Media Rivalry
It’s hard to ignore the timing of Guilfoyle’s post, which seemed to play into a quiet, unspoken competition with Anderson.
Just days earlier, Anderson had shared her own luxurious Valentine’s Day surprise—a package from Portage Foods, known for its premium caviar and smoked fish.
Her caption, ‘Ready for Valentine’s Day,’ was paired with champagne glass emojis and a song titled ‘Caviar and Champagne,’ hinting at an elegant celebration.
The high-end tasting set she received is worth nearly $1,000.
A Look Back at Past Valentine’s Days
Comparisons were quickly drawn between Don Jr.’s new romance and his past relationship with Guilfoyle.
In a 2019 interview, Don Jr. described himself as ‘more of a fisherman than a romantic’ and admitted that their Valentine’s plans were typically low-key.
This year’s celebration with Anderson seems to be taking a more extravagant turn.
Super Bowl Weekend and New Beginnings
Valentine’s Day isn’t the only time Don Jr. and Anderson have been making headlines.
Over the weekend, the couple attended the Super Bowl together, sitting in a VIP box with three of Don Jr.’s five children.
Notably absent from the gathering was his eldest daughter, Kai. Meanwhile, Guilfoyle was also at the game but was seen mingling in different circles.
She shared a cozy snap with Yellowstone star Kevin Costner and posed for photos with comedian Pete Davidson, actor Jaleel White, and Gracie Hunt, the daughter of Chiefs owner Clark Hunt.
Guilfoyle’s New Role and Life After Don Jr.
Since her split from Don Jr., Guilfoyle has remained an influential figure in political circles.
She has been present at several major events tied to Donald Trump’s campaign and was recently appointed as the U.S. Ambassador to Greece.
Trump himself announced her new role shortly after news of her breakup with Don Jr. and his new relationship came to light. Don Jr. publicly supported the appointment, saying, ‘I could not be more proud of her and the important role she’ll continue to play in my father’s administration.’
The Breakup Timeline and a New Chapter
Guilfoyle and Don Jr. started dating in 2018 and got engaged in December 2020.
While the exact timing of their breakup remains unclear, Don Jr. was first seen with Anderson in September 2024, when they were photographed sharing a kiss at a Palm Beach restaurant.
At the time, insiders claimed that Guilfoyle was caught off guard, with one source revealing, ‘Kimberly either didn’t know about Bettina—or didn’t want to know.’
Despite the breakup and public attention surrounding Don Jr.’s new romance, Guilfoyle seems determined to focus on her own future, whether that involves politics, new personal endeavors, or a mysterious new suitor sending her roses from afar.
This article was published on TDPel Media. Thanks for reading!
Share on Facebook «||» Share on Twitter «||» Share on Reddit «||» Share on LinkedIn