Her mother, Bonnie Kay, owned a modeling agency, and her stepfather, Charles Haydon, was a prominent lawyer who had Marilyn Monroe among his clients.
Vanessa's adolescence was filled with luxuries, she received an education in private institutions, and her friends were the young elite of New York. Her high status did not come from her mother but from her father, who had invested 30% in the shares of the Italian products company Rao's Specialty Foods, sold in 2017 for 415 million dollars. The family inherited an incredible fortune when Charles passed away in 2005.
While in high school, Vanessa fell in love with Valentín Rivera, a member of the violent Latin Kings gang whom, according to People magazine, she allegedly helped trade marijuana and even visited him in jail. It is surprising that her next conquest was Leonardo DiCaprio (50), with whom she posed on different red carpets in 1998. Those who know her well claim that Vanessa has been obsessed with being a celebrity since she can remember.
It is known that professionally she worked as a model at the prestigious Wilhelmina agency and even tried her luck as an actress in the movies When Least Expected (2003) and the series The Apprentice (2004), whose star was Donald Trump.
From 1998 to 2001, she dated Prince Khalid bin Bandar bin Sultan Al Saud, from the Al Saud family, one of the wealthiest families on the planet, but they were forced to break up when the young man left the United States after the 9/11 attacks, as his father had been one of the main suspects of the terrorist attack. Subsequent investigations exonerated him.
At a fashion show, Donald Trump (78) approached the young woman to introduce her to his eldest son, Donald Trump Jr., but they did not hit it off until they met again at a mutual friend's birthday party. Some time later, Trump Jr. proposed to her with a $100,000 diamond ring that, by the way, was free for her, as he had made a deal with the jeweler for the proposal with photographers to take place at the store's entrance. In 2003, they got married in a ceremony officiated by Judge Maryanne Trump, the sister of the current president, in a lavish wedding at Mar-a-Lago, the vast estate of the current President of the United States in Florida.
The marriage has produced five children, Kai Madison (17) -publicly supported her grandfather in the presidential campaign-, Donald John (16), Tristan Milos (13), Spencer Frederick (12), and Chloe Sophia (10). The marriage ended in divorce in 2018, a year after Trump was inaugurated as the 45th President of the United States.
Since their breakup, Vanessa has not had any high-profile social relationships until the Daily News published the exclusive about the relationship between Donald Trump's ex-daughter-in-law and Tiger Woods, which the athlete confirmed this weekend.