The Twists and Turns of Vanessa Trump's Love Life
Vanessa Trump never fades from public attention for long, thanks to her remarkable dating history and connections in both celebrity and political circles. The latest headline? She’s confirmed her relationship with golf icon Tiger Woods—a pairing guaranteed to draw stares and speculation. In March 2025, the two posted an affectionate Instagram photo, with Woods writing, “Love is in the air and life is better with you by my side. We look forward to our journey through life together.” The couple also politely asked for privacy, aware of the searing spotlight already on them.
This new relationship feels almost natural if you know their backstory. Vanessa and Tiger reportedly grew close through their kids, who play competitive golf at the same school. Picture these two at youth tournaments, quietly cheering from the sidelines, while their children bonded before their parents ever did.
From Teen Romance to Hollywood and Royalty
Vanessa Trump's love life has always been a little unconventional. Before her recent headline-making romance, she was known for a strikingly diverse list of exes:
- Valentin Rivera (1998–2001): In her teens, Vanessa dated Rivera, a member of the Latin Kings gang. While that chapter is behind her, it’s still surprising to many. Rivera has spoken about their relationship, recalling how Vanessa wrote him letters while he was incarcerated for assault and weapons charges. He claims their romance ended abruptly after she met someone worlds apart from his crowd.
- Leonardo DiCaprio (1998): Rivera wasn't exaggerating. After the breakup, Vanessa was briefly linked to Leonardo DiCaprio. Yes, the Oscar-winning actor. Their relationship was short-lived—a classic New York City fling—yet it was enough to get tabloids buzzing when they attended a high-profile party together.
- Saudi Prince Khalid bin Bandar bin Sultan Al Saud (1998–2001): Not many can claim they dated royalty, but Vanessa can. She reportedly lived with Saudi Prince Khalid bin Bandar, and marriage was even on the cards. But the events of September 11, 2001, forced him to return to Saudi Arabia, effectively closing that royal chapter in her life.
- Donald Trump Jr. (2003–2018): The relationship that made Vanessa a household name. She met Donald Trump Jr. at a fashion show in 2003, introduced by Donald Trump Sr. The couple tied the knot in 2005 at Mar-a-Lago and had five kids together. Their marriage ended in 2018, but they’ve both said their focus remains on co-parenting and their children’s happiness.
Her dating history never fails to catch attention, not just because of the fame attached to her partners, but the sheer variety—from a New York gang member to a Hollywood icon, a Saudi prince, one of America’s most controversial political figures, and now the world-famous golfer Tiger Woods.
Tiger’s own love life has played out under the harshest spotlights too, with very public marriages and breakups involving Elin Nordegren, Lindsey Vonn, and Erica Herman. Both Tiger and Vanessa know what it’s like to have their private matters turned into tabloid fodder, which only adds to the bond they share today.
Friends of Vanessa have remarked that she often ends up with men who are either well-known or have a major presence in some way. But they also point out she’s fiercely protective of her privacy and sees herself, first and foremost, as a mom. These priorities are clear in her relationships—especially now, with two single parents united by their children’s passion for golf.
