Though Trump Jr. has only been married once, he’s been engaged 3 times. About his proposals to ex Vanessa, former Fox News host Kimberly Guilfoyle and Bettina Anderson.
For the third time in his life, Donald Trump Jr. has popped the question — and each time, the answer was yes.
Though the eldest son of President Donald Trump and the late Ivana Trump has only been married once, he’s been engaged three times. Here’s a look back at his proposals to Vanessa Trump, former Fox News host Kimberly Guilfoyle and Palm Beach, Florida, socialite Bettina Anderson.
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).
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.
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 Jan. 12, 2026, Donald Trump Jr. is engaged to Palm Beach socialite Bettina Anderson (see below), 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 Vanessa Trump’s divorce in 2018, Donald Trump Jr. began dating former Fox News host Kimberly Guilfoyle, ex-wife of California Gov. Gavin Newsom.
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 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.
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.
According to a Jan. 12, 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.
Since December 2024, when tabloid photos surfaced of Donald Trump Jr. kissing Bettina Anderson, a model and socialite from Palm Beach, Florida, the pair have been spotted at various Trump family gathering, including presidential events:
Inauguration Day festivities the week of Jan. 20, 2025Super Bowl Sunday LIX in New Orleans, Louisiana, with Donald Trump, Ivanka Trump and her son Theodore “Theo” Kushner, Donald Trump Jr. and three of his children, Eric and Lara TrumpWhite House Easter Egg Roll, hosted by first lady Melania Trump and attended by Donald Trump Jr.’s children with ex-wife Vanessa TrumpDonald Trump’s 79th birthday celebration and U.S. Army 250th anniversary military parade in Washington, D.C., the same weekend as a nationwide anti-Trump “No Kings” mass protestCharlie Kirk’s funeral in Arizona, in which Donald Trump Jr. performed his impression of Donald Trump, voice and mannerisms
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 latest 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.
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.