Love is in the air, for at least one member of the Trump family (yay, I guess). While her former father-in-law is busy stressing out whether he looks hot enough in a random portrait, Vanessa Trump is sowing the seeds of new love. Donald Trump Jr.’s ex-wife is officially dating star golfer Tiger Woods, per a very earnest hard launch Tiger posted to his Instagram.
Tiger posted two pics of the couple posing together, along with the caption: “Love is in the air and life is better with you by my side! We look forward to our journey through life together. At this time we would appreciate privacy for all those close to our hearts.”
Not only does Vanessa’s daughter Kai go to the same school as Tiger’s kids, Charlie and Sam, but Kai is also an avid golfer, so that likely helped Vanessa and Tiger bond.
Before Tiger, Vanessa was obviously Don Jr.’s wife, so we know she has a famous relationship pedigree. But if you dig deeper into her dating history, there are some even wilder finds. I’m talking foreign princes and movie stars wild. Yeah, I had no idea, so please join me on this very necessary deep dive into Vanessa Trumps’ dating history.
Valentin Rivera
For five years when she was a teenager, Vanessa dated alleged Latin Kings gangster Valentin Rivera, according to Page Six. When she was 16 years old, he served a 16-month-sentence in prison for assault, and she wrote love letters to him during their time apart. In one letter, she wrote about how she couldn’t wait to turn 18 because it meant she’d be able to start her life with Valentin. “I can’t wait till that year because a lot’s going to happen,” she wrote. “My 18th birthday, you’ll be back in my arms, my prom, and I want to get pregnant and have a baby with you after January. I want to get pregnant so the baby is born after I graduate since it takes 9 months.”
As we know, life didn’t work out that way for Vanessa and Valentin, but at least they have the letters to remember their young love.
Leonardo DiCaprio
Yep, that’s right, the Leonardo DiCaprio. Valentin actually broke up with Vanessa when she was 20 because he learned that she’d met Leo at a New York club and cheated on Valentin with him. In 1998, New York Magazine reported that Vanessa (whose last name was still Hayden and was working as a model at the time) and Leo were seen together around New York. They never became official, though, so it sounds like it was really just a fling.
A Saudi Prince
Vanessa also allegedly had a pretty serious relationship with Prince Khalid bin Bandar bin Sultan Al Saud, so serious that she wanted to marry him. “They dated from 1998 to 2001 and lived together. He ditched her on 9/11; days after, he flew back to Saudi Arabia. They were planning to marry [at the time]. They were inseparable,” an anonymous source told Page Six.
His father is Bandar bin Sultan Al Saud, who was Saudi Arabia’s ambassador to the US from 1983 to 2005.
Donald Trump Jr.
And then, of course, there’s Don Jr. The two met at a fashion show in 2003 when Don Sr. introduced them. They got engaged in 2004 through a promotional deal with a jeweler at a mall in New Jersey. Yes, seriously. Vanessa’s ring was free in exchange for the free press the store got when Don Jr. proposed right in front of it. Ah, romance!
They got married at Mar-A-Lago in 2005. But after 12 years of marriage and five kids, they called it quits in 2018.
Tiger Woods
This all leads us to Tiger. According to The Daily Mail, Vanessa and Tiger started quietly dating in November 2024. According to an anonymous source, when he called his ex-wife Elin Nordegren to let her know about the relationship: “Her response at first was like ‘Seriously? A Trump? For real?’ But Vanessa’s former sister-in-law Ivanka Trump gave the new relationship her seal of approval with the IG comment: “So happy for you both !”
