Trump Jr., Bettina Anderson relationship timeline: IG official to wedding day

Jennifer Sangalang, USA TODAY NETWORK - FloridaFri, May 22, 2026 at 6:18 PM UTC

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Trump Jr., Bettina Anderson relationship timeline: IG official to wedding day

The world found out about Donald Trump Jr. and Bettina Anderson in December 2024.

Now the couple is set to marry over the 2026 Memorial Day weekend, according to reports.

Though the eldest son of President Donald Trump and the late Ivana Trump has only been married once, he’s been engaged three times. The 48-year-old father of five and his fiance Bettina Anderson, 37, announced their engagement in a White House event in December 2025. Page Six and CNN have reported a destination wedding in the Bahamas for Donald Trump Jr. and the Palm Beach socialite.

Where did the Trump family get married? Most said "I do" at Mar-a-Lago in Florida, Trump's private club

Ahead of their walk down the aisle together, his second and her first, here's a look at the relationship timeline for Donald Trump Jr. and Florida model Bettina Anderson.

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Relationship timeline for Donald Trump Jr. and Bettina Anderson -

In 2024, Donald Trump campaigned for a third time in his second shot at the White House. His son, Donald Trump Jr. had been engaged to former Fox News host Kimberly Guilfoyle, a close Trump ally, since 2020. The couple eventually broke up in 2024, but it is not known when they called off their engagement.

During the 2024 presidential election, Guilfoyle campaigned alongside Donald Trump Jr. and sat in the VIP family box at the Republican National Convention in Milwaukee, Wisconsin, in July 2024. Bettina Anderson also was seated in the VIP family box, next to Guilfoyle's son Ronan Villency, at the 2024 RNC near late wrestling icon and RNC presenter Hulk Hogan (see photo gallery with this story). At the time, it was presumed that Donald Trump Jr. was still engaged to Guilfoyle.

In October 2024, Anderson co-hosted an exclusive VIP Donald Trump fundraising dinner in Palm Beach, Florida.

She also appeared with the extended Trump family ahead of Election Day, Nov. 5, 2024.

However, photos surfaced in early December 2024 of Donald Trump Jr. and the Palm Beach, Florida, socialite holding hands and kissing. Days later, Donald Trump − then president-elect − appointed Guilfoyle as ambassador to Greece. News reports then showed Donald Trump Jr. and Anderson vacationing together abroad, though Guilfoyle was still sporting her engagement ring as seen in a Dec. 17, 2024, social post about her ambassadorship to Greece.

Donald Trump Jr. brought the model and socialite as his date to the family's 2024 New Year's Eve party at Mar-a-Lago.

Anderson attended the Inauguration Day festivities in Washington, D.C., which started Jan. 19, 2025. Though she appeared at the Trump family indoor parade, Donald Trump Jr. danced with his eldest daughter Kai Trump at the Inaugural Ball with Donald and Melania Trump and his siblings and their spouses, Ivanka Trump and Jared Kushner, Eric and Lara Trump and a then-pregnant Tiffany Trump and Michael Boulos. Guilfoyle and Donald Trump Jr.'s ex-wife Vanessa Trump also attended Inauguration Day festivities that week at the White House and in Washington, D.C.

It was not known when Donald Trump Jr. and Kimberly Guilfoyle ended their romantic relationship nor when Donald Trump Jr. and Bettina Anderson began theirs.

Bettina Anderson and Donald Trump Jr. did become "Instagram official" after Super Bowl Sunday LIX in February 2025 in New Orleans, Louisiana.

During her Senate confirmation hearing in July 2025, Guilfoyle was accompanied by her brother, son Ronan Villency, and Donald Trump III aka "Donnie Trump," the eldest boy of Donald Trump Jr. and Vanessa Trump's five children. Guilfoyle was officially confirmed as Greece ambassador in September 2025.

A spokesperson for Donald Trump Jr. confirmed his engagement to Anderson, who has never been married or had children, with USA TODAY on Dec. 16, 2025, two weeks before Trump Jr. turned 48. The pair got engaged at Camp David, the presidential retreat in Maryland.

On April 12, 2026, Anderson held a bridal shower at Mar-a-Lago, Trump's private club, attended by family members Ivanka Trump, Arabella Kushner, Tiffany Trump, Lara Trump and Marla Maples, Donald Trump's second ex-wife and mom to Tiffany.

According to a May 22, 2026, record search, Donald Trump Jr. and Kimberly Guilfoyle's home in Jupiter, Florida, remains off the market and both names appear on property records. Bettina Anderson owns a townhouse in Palm Beach County, Florida.

Donald Trump Jr. and Bettina Anderson are set to marry Memorial Day weekend. The federal holiday is Monday, May 25, 2026.

Contributing: Zac Anderson, USA TODAY

Sangalang is a lead digital producer for USA TODAY Network. Follow her on Twitter or Instagram at @byjensangalang. Subscribe to the free Florida TODAY newsletter.

This article originally appeared on Palm Beach Post: Before Trump Jr., Bettina Anderson wedding, their relationship timeline

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