Donald Trump Jr.’s ex-wife Vanessa Trump has been all over the headlines ever since rumors started swirling that she was in a relationship with Tiger Woods.
Woods confirmed that he was dating Vanessa, 47, in a post shared to Instagram on Monday.
The PGA golfer, 49, included two photos, including one of Vanessa cuddling up next to him with her head on his shoulder as they lay on an outdoor swing, when he launched the relationship.
He captioned the post, “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.”
Woods and Don Jr. may be two of the most well-known Vanessa has been linked to, but they aren’t the only ones.
If you take a closer look, her dating history is quite intriguing – and almost unbelievable.
Here’s an in-depth look at Vanessa’s complete dating journey.
Valentin Rivera
Vanessa’s first serious relationship was with Latin King’s gangster Valentin Rivera.
According to “Page Six,” Vanessa met Rivera, who was in the street and prison gang Latin Kings, when she was a teenager.
Rivera served multiple prison terms for assault, weapons offenses, and negligent homicide, which is what ultimately led to their split.
They broke up five years after being together.
“She was heartbroken that I was being taken away,” Rivera told “Page Six” in 2018. “The first time [she came to visit], she was upset — she cried a little bit — but after a while, we get used to things. She only came to visit me twice because her mother forbid her from coming to visit me.”
The couple’s relationship ended in 1998.
Vanessa was 20 at the time.
Leonardo DiCaprio
There’s no question that Leo loves beautiful women, and Vanessa is one of them – or was at one time.
Woods’ new girlfriend was linked to the “Catch Me if You Can” actor, 50, after she split from Rivera.
The couple was seen snuggling at a premiere party for James Toback’s “Two Girls and a Guy” at the restaurant Momba in New York City in 1998, according to “New York Magazine.”
In May 1998, “Page Six” revealed that the “passionate” couple “tried to keep a tight lid on their budding romance — but it all spilled out during a private party in a trendy SoHo loft … The couple could be seen holding hands, kissing and cuddling into the wee hours in a dimly lit corner.”
“I don’t think it’s a fling,” an acquaintance of Vanessa told the outlet at the time.
Saudi Prince Khalid bin Bandar bin Sultan Al Saud
After her rumored fling with DiCaprio, Vanessa moved on to Saudi prince Khalid bin Bandar bin Sultan Al Saud.
According to “Page Six,” Vanessa and Bandar 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,” a source told the outlet in 2018.
Bandar’s father was Saudi Arabia’s ambassador to the US from 1982 to 2005.
He was suspected to have “indirect ties to al Qaeda and associates of the 9/11 hijackers, but there was no evidence that he knowingly provided support for the attacks,” per the outlet.
Donald Trump Jr.
IMAGN/USA Today
Vanessa went in a completely different direction after splitting from the Saudi prince. Her next crush was on Don. Jr., the eldest son of President Donald Trump.
Vanessa married Don Jr. four years after things ended with Bandar in 2005. The couple wed at Mar-a-Lago in Palm Beach, Florida after meeting at a fashion show in 2006.
They share five children together: Kai, Donald III, Tristan, Spencer, and Chloe.
They divorced in 2018.
Tiger Woods
The PGA golfer is the newest man to be added to Vanessa’s dating roster.
Woods and Vanessa live 20 minutes apart in a southern Florida enclave of Pal Beach, so it should be easy to make the relationship work.
It’s unclear how or when the relationship started. However, Vanessa’s daughter Kai attends school with Woods’ children, Sam and Charlie, and they were friends before the romance started.
Both Kai and Charlie are aspiring golfers. The two of them coincidentally competed in a high-profile junior golf tournament earlier this month.
