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.
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.
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.
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.
