If you’ve been keeping up with the headlines lately, you know the Trump family is basically a walking soap opera. Between the political rallies and the social media firestorms, one name keeps popping up when people look back at the family tree: Vanessa Trump. Honestly, most people just know her as the "ex-wife," but there is way more to the story of who was don jr married to than just a divorce filing in 2018.
Don Jr. didn't just meet a random socialite; he married a woman who had been in the New York spotlight long before she became a Trump. Vanessa Kay Haydon (now Vanessa Trump) was a model, a mother of five, and someone who navigated the intense pressure of the Trump brand for over a decade.
The Meet-Cute That Happened Twice
You’d think the son of a real estate mogul would have a suave "how we met" story. Well, it was actually kinda awkward. Back in 2003, at a fashion show, Donald Trump Sr. himself introduced the two. He literally walked up to Vanessa and said, "Hi, I'm Donald Trump. I wanted to introduce you to my son Donald Trump Jr."
Fast forward five minutes. The elder Trump, apparently forgetting he just did this, walked back up to Vanessa with Don Jr. in tow and tried the same introduction. Vanessa’s response? "Yeah, we just met five minutes ago."
They didn't even hit it off that night. It took a mutual friend’s birthday party a few weeks later for them to actually talk. They talked for an hour, sparks flew, and the rest is history. They got married at Mar-a-Lago in 2005, with Don Jr.’s aunt, Judge Maryanne Trump Barry, officiating.
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Who Is Vanessa Trump, Anyway?
Before she was a Trump, Vanessa was Vanessa Haydon. She grew up on the Upper East Side of Manhattan—very posh, very New York. Her mother, Bonnie Kay Haydon, ran a modeling agency called Kay Models, so it’s no surprise Vanessa ended up in front of the camera. She was signed to Wilhelmina Models and even had a tiny role in the 2003 movie Something's Gotta Give.
But here’s the wild part: her dating history before Don Jr. reads like a celebrity tabloid.
- She dated a local street gangster named Valentin Rivera in her teens (yes, really).
- There were rumors she dated Leonardo DiCaprio.
- She had a three-year relationship with a Saudi prince, Khalid bin Bandar bin Sultan Al Saud.
Basically, she was used to the "high-profile" life. When she married Don Jr., she didn't just become a wife; she became a core part of the Trump machine.
Life as a Trump: Five Kids and a Growing Business
During their 12-year marriage, the couple had five children: Kai, Donald John III, Tristan, Spencer, and Chloe. You’ve probably seen Kai Trump lately; she’s 18 now and making waves as an avid golfer and speaker.
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Vanessa wasn't just sitting at home, though. She launched her own line of handbags called La Poshett and appeared on The Apprentice a few times. For a long time, they seemed like the "stable" couple in the family. But as the 2016 election ramped up and the spotlight got hotter, things started to crack.
Why the Marriage Ended
In March 2018, Vanessa filed for an uncontested divorce. People were shocked, but insiders said it had been coming for a while.
Why did it happen? There wasn't just one reason. Rumors of Don Jr.’s infidelity swirled for years. Some reports suggested the strain of the presidency and the constant media scrutiny were too much. Interestingly, there was also talk about a "life-changing" inheritance Vanessa received from her father’s investments, which some say gave her the financial independence to finally walk away.
By the end of 2018, the divorce was finalized. They’ve stayed surprisingly amicable, though, often spending holidays together for the sake of the kids.
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Where Are They Now? (The 2026 Update)
If you’re wondering who was don jr married to in terms of current status, the landscape has changed significantly. Don Jr. moved on to a high-profile relationship with Kimberly Guilfoyle, but that recently ended.
As of late 2025, Don Jr. is actually engaged to Bettina Anderson, a Palm Beach socialite. They made it official during a Christmas reception at the White House, with the President himself sharing the news.
And Vanessa? She’s doing just fine. In early 2025, she made headlines when it was revealed she is dating golf legend Tiger Woods. They reportedly met through their children (Tiger’s son Charlie and Vanessa’s kids are all in the golf circuit) and have been together since late 2024.
Actionable Takeaways for Following Celeb News
- Check the Timeline: Celebrity relationships in the Trump orbit move fast. What was true in 2024 (like the Guilfoyle engagement) changed by 2026.
- Look Beyond the Name: Vanessa Trump’s story shows that many "political spouses" have deep professional and personal histories long before they enter the public eye.
- Follow the Kids: Often, the best way to see how ex-couples are getting along is by looking at their shared parenting—Vanessa and Don Jr. are still frequently seen at the same events for their five children.
Vanessa Trump might have started as a model and ended up a member of a political dynasty, but her move away from that world into a private life with one of the greatest golfers of all time is a plot twist nobody saw coming.