For the third time in his life, Donald Trump Jr. found a partner in marriage − and recently, they said, “I do.”
President Donald Trump’s oldest son, Donald Trump Jr., tied the knot with Florida socialite Bettina Anderson on Thursday, May 21, according to a Palm Beach County marriage license obtained by USA TODAY.
The couple is also set to hold a ceremony during Memorial Day weekend, though the groom’s father announced on Friday, May 22, that he would not be able to attend, saying he felt compelled to stay in Washington, D.C.
Donald Trump Jr., the 48-year-old father of five and his new bride Bettina Anderson had announced their engagement in a White House event in December 2025. Page Six and CNN previously reported the wedding was 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
Donald Trump Jr., Bettina Anderson are married ahead of Memorial Day 2026
Donald Trump Jr., the eldest son of Donald and the late Ivana Trump, tied the knot with Bettina Anderson on Thursday, May 21, according to a Palm Beach County, Florida, marriage license obtained by USA TODAY.
Here’s a look back at Donald Trump Jr.’s proposals to Vanessa Trump, former Fox News host Kimberly Guilfoyle and 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).
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 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: