President Donald Trump's oldest son, Donald Trump Jr., is engaged to Bettina Anderson, who has said she felt "like the luckiest girl in the world."

On March 13, 2025, news reports suggested Tiger Woods was dating Vanessa Trump, former daughter-in-law of his friend Donald Trump. Donald Trump Jr. and Vanessa Trump’s eldest child, daughter Kai Madison Trump, attends the same school as Tiger Woods' son, Charlie Woods.

A secretive members-only club tied to Donald Trump Jr. is drawing new scrutiny after former staffers described a closed-door world of extravagant spending, rigid security, and strict loyalty rules. The Executive Branch club operates behind an unmarked entrance in Georgetown and caters to a small roster of high-ticket members drawn from the MAGA orbit and business elite.