Donald Trump Jr. and Bettina Anderson are reportedly preparing for a Memorial Day weekend wedding in Palm Beach, according to entertainment media reports and growing speculation circulating through South Florida's political and social circles.
While neither Trump Jr. nor Anderson has publicly confirmed the plans, reports from outlets including Page Six say preparations and invitations tied to a possible wedding celebration are already underway, potentially setting up one of the most closely watched Trump family gatherings since Donald Trump returned to the White House earlier this year.
The rumored ceremony would place Palm Beach and Mar-a-Lago once again at the center of the Trump family's political and social universe, blending Republican power brokers, wealthy donors and high-profile celebrity guests into what insiders describe as a potentially massive Memorial Day weekend event.
Trump Jr., 48, and Anderson first became publicly linked in 2024 after appearing together repeatedly at events in Florida and New York. Their relationship quickly attracted attention beyond tabloid coverage because Anderson comes from a prominent Palm Beach family deeply connected to the local philanthropy and charity scene.
Over the past year, Anderson has increasingly appeared alongside Trump family members at political events, dinners and celebrations tied to the president's political comeback campaign. She was frequently spotted at Mar-a-Lago gatherings during the 2024 election cycle and at several events connected to the administration's return to Washington.
The reported wedding would mark Trump Jr.'s second marriage. He was previously married to Vanessa Trump, formerly Vanessa Haydon, in a high-profile 2005 ceremony held at Mar-a-Lago. The former couple share five children.
Vanessa Trump has since entered a relationship with Tiger Woods, according to previous reports tied to the Palm Beach social circuit.
Before dating Anderson, Trump Jr. was engaged to former Fox News host Kimberly Guilfoyle. Their split became public shortly before his relationship with Anderson emerged. Guilfoyle now serves as U.S. ambassador to Greece.
The timing of the rumored ceremony is particularly notable given the political calendar. Republicans are already intensifying preparations for the 2026 midterm elections, and Palm Beach has increasingly evolved into a hybrid political and social headquarters for Trump allies, donors and administration figures.
Since leaving Washington in 2021 and later returning to the White House, President Trump has continued using Mar-a-Lago as both a private residence and an informal political operations center. The property has hosted campaign strategy sessions, donor events, holiday parties and several Trump family celebrations over the past few years.
Sources familiar with Palm Beach social circles told entertainment outlets the possible wedding guest list could include politicians, athletes, celebrities and major Republican financiers, further reinforcing the Trump family's role at the center of conservative political culture and elite Florida society.
