Vanessa Trump has kept a relatively low profile since divorcing Donald Trump Jr. in 2018. She was quietly supporting her former father-in-law Donald Trump and raising the five children she shares with her ex — Kai, 17, Donald III, 16, Tristan, 13, Spencer, 12, and Chloe, 10 — in the background.
Followers of the Trump family might consider her a very private person, but her dating history proves that she doesn’t shy away from high-profile men. By now, the world knows about her confirmed romance with Tiger Woods after he posted an Instagram official snapshot. “Love is in the air and life is better with you by my side! We look forward to our journey through life together,” the legendary golfer wrote in the caption. “At this time, we would appreciate privacy for all those close to our hearts.”
Woods and Donald Jr. aren’t the first bold-faced names she’s reportedly dated either. She may keep quiet about her private life, but the mom of five is attracted to the spotlight. The 47-year-old former model’s first boyfriend, Valentin Rivera, was a part of the Latin Kings gang. According to the Daily Mail, they dated for five years while they were in school together in New York City.
Even when Rivera served 16 months in prison for assault, Vanessa reportedly stood by his side. Page Six obtained her handwritten letter to her then-boyfriend from Dec. 13, 1993. She wrote, “I miss you a lot, especially since it’s my birthday coming up. And I wish you were here to celebrate with me. But you’ll be out [of prison] for my 18th birthday.” The couple dated until she was 20 when she allegedly had a fling with Leonardo DiCaprio.
The Leonardo DiCaprio situation
In 1998, Vanessa was spotted by Star Magazine, via New York Magazine, “nuzzling” DiCaprio at the premiere party for Two Girls and a Guy. “Leonardo DiCaprio has fallen hard for a stunning young model — and pals say this time it’s love. The superstar is so smitten with blonde beauty Vanessa Haydon (her maiden name) that he’s now a one-woman man,” the source said. DiCaprio’s publicist Cindy Guagenti refuted the rumor, and a former classmate told the NY outlet, “Vanessa played the media really well.” He claimed that she went from “a total gangster bitch” to “all dolled up and ladylike.” A Manhattan socialite was born!
From there, Vanessa moved on to Prince Khalid bin Bandar bin Sultan Al Saud for a three-year romance that lasted until just after Sept. 11, 2001, when he was forced to leave the U.S. By 2003, her destiny was set when the future president introduced her to Donald Jr. “I’m at this fashion show,” Vanessa told The New York Times in a 2006 interview. “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.”
That fateful meeting led her down the aisle in 2005 and eventually brought her to Woods. Vanessa might be a quiet public figure, but she doesn’t mind dating a man in the spotlight.
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