Vanessa Trump's Past Relationships Prove She Really Doesn't Have A Type

It'd be hard to pin down what exactly Vanessa Trump looks for in a partner based on her dating history alone, as many of her reported romances couldn't have been anymore different from each other. If someone knew Vanessa back in her more formative years, for instance, they might've assumed she gravitated towards bad boys.

Her first serious relationship was with Valentin Rivera, who used to be a member of the Latin Kings gang in New York. Although they met in the fifth grade, they didn't start dating until they were 15. Rivera would find himself getting deeper into the street life, which, in turn, made Vanessa fall even deeper in love with him. "She was fascinated. We were kids. She liked the street life at the time," Rivera said in an interview with Page Six. "She liked that type of environment — being around gang members and stuff."

The pair's relationship ended when Rivera discovered that she was allegedly having an affair with actor Leonardo DiCaprio in 1998. Rivera was left heartbroken by the news, even joking that he considered getting back at DiCaprio for dating his girlfriend at the time. But Trump's brief reported relationship with the "Titanic" star hinted at the wide range of men she'd attach herself to. After DiCaprio, Vanessa dated Saudi Prince Khalid bin Bandar bin Sultan Al Saud from 1998 to 2001. But Bandar left the country due to the pressure his family faced after the September, 11, 2001 terrorist attacks.

For a while, it looked like Vanessa Trump found her true soulmate in Donald Trump. Jr. The two met at a New York fashion show in 2003, but didn't officially start dating a few weeks later after reuniting at a birthday party. They eventually married in 2005 and had five children together. They enjoyed 12 years of marriage before announcing their divorce in 2018.

Although neither has given a specific reason for their relationship falling apart, an insider claimed that Donald Jr.'s lack of financial support caused the rift between them. "He gives her very little help and has been keeping her on a tight budget," a source said to Page Six. "She doesn't live a lavish life and can very rarely pick up a check at dinner." Since their divorce, Vanessa has maintained a low profile, but she still seems to surprise people with her potential dating candidates.

Vanessa was spotted driving around with a Secret Service agent she'd met back when her father-in-law, president-elect Donald Trump, was still in the White House. The February, 2024 sighting showed the pair on a casual outing with Vanessa's 12-year-old son, Tristan, sparking rumors that they might've been an item. But whether there's any truth to the rumors is anyone's guess, as there's been little update on her relationship status. At any rate, whoever Vanessa might wind up dating next, her history has shown it won't be a choice that anyone will see coming.