In another witty caption, Anderson added: “I fell for his heart… and bounced right back.”
Trump Jr. responded in kind, reposting the photo and tagging clothing brand American Eagle. He teased: “Yo, @americaneagle—call me!” The move was a playful nod to the company’s recent high-profile denim campaign featuring actress Sydney Sweeney, which had already stirred plenty of conversation online.
Hours later, Anderson fueled the lighthearted banter with a photoshopped image of Trump Jr. in a full denim outfit—often dubbed a “Canadian tuxedo”—tagging the brand once again with the caption: “My guy… get at us @AmericanEagle.”
Beyond the laughs, Anderson herself has drawn attention for her background. Educated at Columbia University and active in environmental philanthropy, she is frequently described as one of Palm Beach’s most prominent social figures. Her relationship with Trump Jr. first surfaced publicly at last summer’s Republican National Convention, and since then, the couple has been spotted together at a variety of events.
Trump Jr., who was previously engaged to Kimberly Guilfoyle, has kept his private life relatively quiet since their split. But with Anderson, he appears to be embracing a more playful and lighthearted chapter—one where even an internet joke can be turned into a fun moment between them.
Whether American Eagle responds to the callout or not, one thing is clear: Trump Jr. and Anderson have shown they’re more than capable of laughing at themselves while keeping the spotlight firmly in stride.
Sometimes the best way to handle unexpected attention is with a sense of humor—and this couple has mastered it. What do you think of their playful approach?