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Vanessa Trump Confirms Relationship with Tiger Woods: A Look at Her Dating History
Vanessa Trump, a prominent socialite with a well-documented romantic past that extends prior to her marriage with Donald Trump Jr., has officially confirmed a new relationship. The former wife of Donald Trump Jr. recently acknowledged her connection with celebrated PGA champion Tiger Woods, who publicly addressed the developing romance in a March 2025 Instagram post.
In his social media announcement, Woods conveyed his affection, stating, “Love is in the air and life is better with you by my side!” He further expressed optimism about their shared future and requested privacy, adding, “We look forward to our journey through life together. At this time, we would appreciate privacy for all those close to our hearts.”
Prior to her relationship with Tiger Woods and her decade-long marriage to Donald Trump Jr., Vanessa Trump’s past romantic connections have garnered media attention, particularly a rumored liaison with Hollywood megastar Leonardo DiCaprio. A retrospective look at her dating history follows below.
Valentin Rivera
Vanessa Trump’s earliest publicly documented romantic involvement was reportedly with Valentin Rivera, identified as an alleged member of the Latin Kings gang, during her teenage years. Sources indicate that the relationship spanned five years, during which time Vanessa Haydon, as she was then known, corresponded with Rivera while he was incarcerated for a 16-month prison sentence.
Leonardo DiCaprio
Reports suggest a brief connection with actor Leonardo DiCaprio in 1998 following their appearance at a premiere party. While neither party publicly confirmed the rumored romance, accounts indicate DiCaprio ended the association when Vanessa was 20 years old, after learning of an alleged infidelity involving Rivera.
Prince Khalid bin Bandar bin Sultan Al Saud
Vanessa Trump was also reportedly linked to Prince Khalid bin Bandar bin Sultan Al Saud. Sources indicate that the pair considered marriage, but the relationship concluded following the events of September 11, 2001. Neither party has issued public statements regarding these reports.
Donald Trump Jr.
Vanessa Trump’s relationship with Donald Trump Jr. commenced in 2003, reportedly initiated by an introduction at a fashion event by Donald Trump Sr. The couple became engaged in 2004, marked by a reported $100,000 engagement ring, and married in 2005. During their twelve-year marriage, they had five children.
In 2017, Vanessa Trump initiated divorce proceedings. The couple publicly announced their separation, emphasizing their commitment to co-parenting, stating, “After 12 years of marriage, we have decided to go our separate ways… 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
Rumors of a relationship between Vanessa Trump and Tiger Woods circulated in early 2025, culminating in their public confirmation in March of the same year.