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Golf icon Tiger Woods, known for fiercely guarding his private life, has confirmed his relationship with Vanessa Trump, the ex-wife of Donald Trump Jr.
In a post on X (formerly Twitter), Woods shared his feelings about his new relationship, writing, “Love is in the air and life is better with you by my side.” The caption accompanied two photos of himself with Vanessa Trump, signaling their official announcement. He also requested privacy for their loved ones, stating, “At this time, we would appreciate privacy for all those close to our hearts.”
Social Media Announcement Follows Weeks of Speculation
The post follows weeks of tabloid speculation about Woods and Vanessa Trump. In what appeared to be a coordinated announcement, Vanessa also shared a picture of the couple on her Instagram account.
Before her relationship with Woods, Vanessa Trump was married to Donald Trump Jr. for over a decade. The two wed in 2005 and separated in 2018, with Vanessa filing for divorce on March 15, 2018. The divorce was finalized later that year.
Who is Vanessa Trump?
Born in 1977, Vanessa Kay Pergolizzi grew up in Manhattan’s Upper East Side. Her mother, Bonnie Kay Haydon, ran the modeling agency Kay Models, while her stepfather, Charles Haydon, was a lawyer. She attended The Dwight School, a private preparatory school in Manhattan, where she excelled as a tennis player. Vanessa later pursued psychology studies at Marymount College in Manhattan.
Vanessa Trump: Dating History
Vanessa’s romantic history has made headlines over the years. While in school, she was involved with Valentin Rivera, a local street gang member, and the two even attended her senior prom together. Rivera later served a 16-month prison sentence for assault.
During her modeling career in her teens and early 20s, Vanessa briefly appeared in the 2003 film Something’s Gotta Give. She was also rumored to have had a connection with Hollywood star Leonardo DiCaprio. According to New York Magazine, she was “seen nuzzling” DiCaprio at a 1998 premiere party, though his publicist denied any romantic involvement.
From 1998 to 2001, Vanessa dated Saudi Prince Khalid bin Bandar bin Sultan Al Saud, son of then-Saudi Arabian ambassador to the U.S., Bandar bin Sultan Al Saud.
How She Met Donald Trump Jr.
Vanessa’s introduction to Donald Trump Jr. was orchestrated by his father, Donald Trump, at a fashion show in 2003. Recalling the moment in a 2006 interview with The New York Times, Vanessa said, “I’m at this fashion show. Donald Trump comes up to me with his son: ‘Hi, I’m Donald Trump. I wanted to introduce you to my son Donald Trump Jr.'”
Minutes later, Trump reintroduced them, seemingly forgetting their earlier interaction. Vanessa humorously recalled telling him, “Yeah, we just met five minutes ago.”
The two, however, didn’t immediately connect. It was only weeks later, at a mutual friend’s birthday party, that they struck up a conversation that lasted for an hour. Their relationship blossomed, leading to an engagement two years later.
Marriage and Family Life
In 2005, Vanessa and Donald Trump Jr. married at Trump’s Mar-a-Lago resort in Florida. Over the years, they welcomed five children: Kai, Donald John III, Tristan, Spencer, and Chloe.
Their eldest daughter, Kai Trump, 17, has followed in her grandfather’s footsteps as an avid golfer. In 2024, she committed to playing for the University of Miami. She also spoke at the Republican National Convention that year and attended her grandfather’s presidential inauguration in January 2025.
Separation and Divorce
Vanessa filed for divorce from Donald Trump Jr. in March 2018 in what was initially an “uncontested” proceeding. However, reports later suggested the divorce became contested, indicating some disagreements over the terms.
In a joint statement at the time, the former couple emphasized their commitment to their children, saying, “We have five beautiful children together, and they remain our top priority.”
By July 2018, Vanessa and Donald Jr. had settled child custody arrangements, and their divorce was finalized by the end of the year.
Speculation Around the Divorce
While the exact reasons behind their divorce were never publicly disclosed, media reports speculated on various factors. One significant theory suggested that Vanessa’s decision was influenced by a financial windfall her family received.
Additionally, rumors circulated about Donald Trump Jr.’s alleged infidelity, with reports suggesting he began dating former Fox News anchor Kimberly Guilfoyle shortly after his divorce was finalized.
Despite their separation, Vanessa and Donald Trump Jr. have maintained an amicable relationship, often appearing together at Mar-a-Lago and various official events.
