With a public declaration of love, Vanessa Trump and Tiger Woods made their relationship official just a few days ago. Reason enough to take a look at the men the model loved before the golf star.
Vanessa Trump, 47, and golf superstar Tiger Woods, 49, just went public with their relationship, and the headlines are already exploding. Two big names are coming together—along with two turbulent love lives, full of missteps.
As the ex-daughter-in-law of former U.S. President Donald Trump, 78, Vanessa Trump has already experienced quite a lot. Her marriage to Donald Trump Jr., 47, lasted from 2005 to 2018, producing five children. But even before her divorce from the president’s son, the stunning Vanessa had been actively dating.
Vanessa Trump: The Men She Loved Before Tiger Woods
As a teenager, Vanessa reportedly dated her classmate Valentin Rivera, according to the Daily Mail. The blonde beauty was in love with the future gang member of the Latin Kings for five years before a 16-month prison sentence tore them apart. In a 1993 letter quoted by the newspaper, the lovestruck 16-year-old spoke of a future together, attending Prom Night (the American high school graduation dance), and her desire to have a baby with Rivera. When Vanessa turned 20, they finally broke up for good.
Love is in the air and life is better with you by my side! We look forward to our journey through life together. At this time we would appreciate privacy for all those close to our hearts. pic.twitter.com/ETONf1pUmI
— Tiger Woods (@TigerWoods) March 23, 2025
Afterward, according to the newspaper, Vanessa claimed to have gotten suspiciously close to Hollywood superstar Leonardo DiCaprio. Shortly after breaking up with her first love, she allegedly had an affair with the Oscar winner. In 1998, New York Magazine reported on the rumored new couple, though DiCaprio’s spokesperson consistently denied any romantic involvement.
A Prince and Donald Trump Jr.
According to the British tabloid, after her Hollywood flirtation, Vanessa dated actual royalty. Prince Khalid bin Bandar bin Sultan Al Saud of Saudi Arabia was reportedly her partner for nearly three years. The couple even lived together in the United States, planned to marry, and were considered “inseparable.” However, after the terrorist attacks of September 11, 2001, the Saudi prince left the U.S., leading to their breakup.
Just four years later, the time had come: Vanessa Haydon walked down the aisle. Her chosen one? Billionaire’s son Donald Trump Jr. The couple said “I do” in a lavish ceremony at the Trump estate, Mar-a-Lago, in Palm Beach. Five children later, they divorced in 2018.
Now, Vanessa Trump has found love again—with golfer Tiger Woods. He, too, has a turbulent past, admitting to numerous extramarital affairs and drug-related offenses. One can only hope that the two have now found happiness together.
