Trump Jr. engagements include Vanessa, Kimberly Guilfoyle, Bettina Anderson
Trump Jr. engagements include Vanessa, Kimberly Guilfoyle, Bettina Anderson
Jennifer Sangalang, USA TODAY NETWORK - FloridaFri, May 22, 2026 at 6:30 PM UTC
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For the third time in his life, Donald Trump Jr. found a partner in marriage − and soon, they'll say, "I do."
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 fiance Bettina Anderson announced their engagement in a White House event in December 2025. Page Six and CNN have reported the wedding is scheduled for the 2026 Memorial Day weekend in the Bahamas.
A look back: Trump Jr. wedding in Bahamas? Most family members married at Mar-a-Lago
Ahead of his upcoming wedding, here’s a look back at his proposals to Vanessa Trump, former Fox News host Kimberly Guilfoyle and Palm Beach socialite Bettina Anderson.
Trump Jr. proposed to Vanessa Haydon outside jewelry store to get $100,000 engagement ring for free
Being the son of a billionaire reality TV star has its perks: Though Donald Trump Jr. enjoyed fame as the eldest son of "Apprentice" star Donald Trump, he cashed in on an opportunity for a free engagement ring − and ensuing media coverage.
Donald Trump introduced Donald Trump Jr. to his future wife at a fashion show in 2003.
In November 2004, Donald Trump Jr. proposed to his then-girlfriend of 1 1/2 years, model Vanessa Kay Haydon, outside of a jewelry store at a New Jersey mall. At the time, Haydon, formerly known as Vanessa Kay Pergolizzi before taking her stepfather's last name, had appeared in the 2003 Jack Nicholson-Diane Keaton film "Something's Gotta Give" and a Third Eye Blind music video.
While dating Haydon, Trump Jr. had appeared on his father's hit reality show "The Apprentice" on NBC with his siblings, Ivanka Trump and Eric Trump, and his future mother-in-law, Melania Knauss. The celebrity couple were preparing to attend Donald Trump's upcoming wedding (in January 2005) to the Slovenian model at his private club, Mar-a-Lago in Palm Beach, Florida. Donald Trump Jr. was the best man.
On Nov. 11, 2004, Donald Trump Jr. popped the big question to Haydon. Both were 26 years old.
According to a 2004 story in the New York Post, because Donald Trump Jr. proposed outside of a jewelry store at Short Hills Mall in New Jersey, he got the $100,000 Bailey Banks and Biddle Fine Jewelers diamond engagement ring for free.
However, the New York Post report adds, Haydon "appeared to enjoy her moment in the spotlight, and revealed that she burst out crying when Donald Jr. popped the question for real in their West Side pad two months ago" or (in September 2004).
Who attended Donald Jr. and Vanessa Trump's Mar-a-Lago wedding
Donald Trump Jr. and Vanessa Haydon were married Nov. 12, 2005, at Mar-a-Lago in front of about 370 guests, reports show, with the service officiated by Donald Trump's sister, Judge Maryanne Trump Barry. Donald Trump Jr. and Vanessa Trump were 27 years old when they wed, weeks before they both turned 28 in December 2005.
Donald Trump Jr.'s siblings were in the wedding party: Ivanka Trump was a bridesmaid, and Eric Trump was a groomsman. At the time, his father and new stepmother, Melania Trump, were newlyweds and expecting a baby − Barron Trump, who was born in March 2006. Donald Trump and his second ex-wife, Ivana Trump, attended the wedding. Ivana is the mother of Donald Jr., Ivanka and Eric Trump.
Vanessa Trump and Donald Trump Jr. had five children together − Kai Trump, Donald Trump III, Tristan Trump, Spencer Trump and Chloe Trump − before they eventually divorced, after 12 years of marriage, in 2018.
As of May 22, 2026, Donald Trump Jr. is set to marry Palm Beach socialite Bettina Anderson (see below) over the Memorial Day weekend, and Vanessa Trump is dating golf legend Tiger Woods, a close friend of Donald Trump and a favorite golf player of Donald Trump Jr. and Vanessa Trump's eldest child, Kai Trump. Vanessa Trump and Tiger Woods hard-launched their relationship in an Instagram post on March 23, 2025. Their children − Kai Trump, Sam Alexis Woods and Charlie Axel Woods − attended the Benjamin School together in Palm Beach County, Florida.
After Trump Jr. proposed to Kimberly Guilfoyle, celebrity couple had multiple anniversary dates
After Vanessa Trump's divorce in 2018, Donald Trump Jr. began dating former Fox News host Kimberly Guilfoyle, ex-wife of California Gov. Gavin Newsom.
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The couple eventually became engaged and bought a home together in Admirals Cove, an exclusive neighborhood in Jupiter, Florida. Guilfoyle was a key member of Donald Trump's re-election campaigns in 2020 and 2024.
Reports state Donald Trump Jr. became engaged to Kimberly Guilfoyle on New Year's Eve, Dec. 31, 2020, although news of their engagement became public in 2022.
Throughout their courtship, the couple appeared to celebrate multiple anniversary dates, though they never specified what the anniversaries were for. It's possible the anniversaries reflect the date of their engagement and when they officially became a couple:
On April 24, 2021, Guilfoyle acknowledged her three-year anniversary with Donald Trump Jr. in a post on Instagram: “Happy Anniversary to my love! The past 3 years have been amazing, filled with adventure and memories that will last a lifetime Here’s to many, many more”
On Feb. 14, 2022, Guilfoyle called Donald Trump Jr. her fiance (and her “forever guy” in a Valentine’s Day post (though on Jan. 1, 2022, after his New Year’s Eve birthday, she referenced spending their lives together and she sported a ring on that finger in a separate Instagram post).
On Dec. 31, 2022, Guilfoyle posted birthday wishes and a happy anniversary note to Donald Trump Jr.: “You are my treasure! Love you to the moon and back. … XO KG and Don”
Through six years and multiple mystery anniversary dates, Donald Trump Jr. and Kimberly Guilfoyle eventually broke up in 2024, but it is not known when the couple called off their engagement.
In spring 2024, Guilfoyle gushed about her relationship with the then-former president's son.
During the 2024 presidential election, Guilfoyle campaigned alongside Donald Trump Jr. and sat in the VIP family box at the 2024 Republican National Convention in Milwaukee, Wisconsin. 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 Palm Beach, Florida, socialite Bettina Anderson 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. The eldest Trump son, meanwhile, brought the model and socialite as his date to the family's 2024 New Year's Eve party at Mar-a-Lago and to the Inauguration Day festivities in Washington, D.C., a month later.
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.
Before the presidential election, Anderson had co-hosted a Donald Trump fundraising dinner in October 2024 in Palm Beach. Months before that, she, too, was seated in the VIP family box, next to Guilfoyle's son Ronan Villency, at the 2024 Republican National Convention, near late wrestling icon and RNC presenter Hulk Hogan (see photo with this story). At the time, it was presumed that Donald Trump Jr. was still engaged to Guilfoyle.
Super Bowl date makes Donald Jr. and Bettina official
Bettina Anderson and Donald Trump Jr. did become "Instagram official" after Super Bowl Sunday LIX in February 2025 in New Orleans, Louisiana. The pair attended the game with Donald Trump, Ivanka Trump, Eric and Lara Trump, and three of Donald Trump Jr.'s children with ex-wife Vanessa Trump.
Trump Jr. announced proposal to Bettina Anderson at White House holiday party
Since December 2024, when tabloid photos surfaced of Donald Trump Jr. kissing Bettina Anderson, the pair have been spotted at various Trump family gatherings, including high-profile presidential events.
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. Donald Trump Jr. and Anderson were widely rumored to be a couple more than a year before that, though his split from ex-fiancée, now U.S. Ambassador to Greece Kimberly Guilfoyle, had not been confirmed at the time.
President Donald Trump announced his son's engagement at a White House holiday party Dec. 15, 2025, according to a video posted to social media by Laura Loomer.
"I just want to wish all of you guys an incredible holiday season ... and to thank Bettina for that one word, 'yes,'" Trump Jr. said in the video.
"This has really been the most unforgettable weekend of my life, and I get to marry the love of my life, and I feel just like the luckiest girl in the world," Anderson said.
Republican presidential nominee and former U.S. President Donald Trump, Vice Presidential Nominee Senator J.D. Vance (R-OH), Usha Chilukuri Vance, Donald Trump Jr., Ivanka Trump, Tiffany Trump, Vanessa Haydon, Chloe Trump, Lara Trump, Eric Luke Trump and Hulk Hogan sit on Day 4 of the Republican National Convention (RNC), at the Fiserv Forum in Milwaukee, Wisconsin, July 18, 2024.
Contributing: Kinsey Crowley, USA TODAY
Sangalang is a lead digital producer for USA TODAY Network. Follow her on Twitter or Instagram at @byjensangalang. Support local journalism. Subscribe to the free Florida TODAY newsletter.
This article originally appeared on Palm Beach Post: Trump Jr., Bettina Anderson to marry. About his past wedding proposals
Source: “AOL Entertainment”
