Vanessa Trump’s Dating History: Her Ex-Boyfriends Before Don Jr.
Now that Vanessa's relationship with Tiger Woods has been confirmed, we're taking a look through her past relationships.
ShanonG
Vanessa Trump has had a high-profile dating history, and it goes back long before she met her ex-husband, Donald Trump Jr. Now, she has a brand-new love. The socialite recently confirmed her relationship with PGA champion Tiger Woods, who shared an Instagram post in March 2025 acknowledging the romance rumors.
“Love is in the air and life is better with you by my side!” Tiger captioned his carousel, which featured photos of him and Vanessa together. “We look forward to our journey through life together. At this time, we would appreciate privacy for all those close to our hearts.”
Before Tiger, Vanessa was married to Don Jr. for just over a decade. However, her relationships beforehand have also made headlines, especially her rumored connection with A-list actor Leonardo DiCaprio. Look back at Vanessa’s dating history below.
Valentin Rivera
Vanessa’s first publicly known romance was with alleged Latin Kings gangster Valentin Rivera when she was a teenager. According to Page Six, Vanessa, whose last name was Haydon at the time, dated Valentin for five years and sent him love letters while he served a 16-month prison sentence.
Leonardo DiCaprio
According to New York magazine, Vanessa was spotted with Leo at a premiere party in 1998, but it only seemed to be a brief connection. The duo never publicly addressed their rumored romance, but according to Betches, the Titanic movie star broke things off with Vanessa when she was 20 after he found out that she allegedly cheated on Valentin with Leo.
Prince Khalid bin Bandar bin Sultan Al Saud
Page Six reported that Vanessa was once linked with a Saudi prince, and they planned on getting married but ended their relationship following the September 11, 2001, attacks. Neither of them publicly commented on the report.
Donald Trump Jr.
In 2003, Vanessa and Don Jr. were introduced to each other at a fashion show by his father, Donald Trump Sr. By 2004, they were engaged, with Don Jr. popping the question with a $100,000 engagement ring. After marrying in 2005, Vanessa and Don Jr. welcomed five children together.
Twelve years later, Vanessa filed for divorce from Don Jr., and they split but vowed to be dedicated co-parents to their kids.
“After 12 years of marriage, we have decided to go our separate ways,” Vanessa and Don Jr. said in a statement at the time, per PEOPLE. “We will always have tremendous respect for each other and our families. We have five beautiful children together and they remain our top priority. We ask for your privacy during this time.”
Tiger Woods
In early 2025, multiple outlets reported that Vanessa and Tiger were dating, but they didn’t confirm the rumors until that March.
