If you’ve spent any time scrolling through political Twitter or catching the evening news over the last decade, you’ve probably seen Don Jr. right in the thick of it. He’s the eldest son, the vocal surrogate, and a constant fixture in the Trump orbit. But away from the rallies and the boardroom, folks are often curious about his personal life. Specifically, they want to know: how many times has Donald Trump Jr been married?
Actually, the answer is simpler than the headlines might make it seem. Donald Trump Jr. has been married exactly one time. That marriage was to Vanessa Haydon (now Vanessa Trump), and it lasted for over a decade. While his romantic life has been a major tabloid fixture—especially with his high-profile engagement to Kimberly Guilfoyle and his recent 2025 engagement to Bettina Anderson—he’s only actually walked down the aisle once.
The Long Road with Vanessa Trump
Don Jr. met Vanessa Haydon back in 2003. Legend has it his father, Donald Trump, actually introduced them—twice—at a fashion show. Kinda awkward, right? But it worked. They hit it off and eventually got hitched on November 12, 2005. The wedding was a massive affair at Mar-a-Lago, which seems to be the family's go-to spot for big milestones.
For a long time, they were the "stable" couple of the Trump family. They had five kids together: Kai, Donald III, Tristan, Spencer, and Chloe. You’ll often see them in family photos, and by all accounts, they are very focused on co-parenting these days.
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But things started to fray around the time the political spotlight got really hot. In March 2018, Vanessa filed for an uncontested divorce. Honestly, the rumor mill went wild. Some said it was the pressure of the "Russia investigation" or the 24/7 security detail that comes with being the President's son. Others pointed to Vanessa inheriting a massive sum of money from her family's marinara sauce business (Rao's), which reportedly gave her the financial independence to move on. Whatever the catalyst, they finalized everything by the end of 2018. They’ve stayed surprisingly friendly since, which is rare in the world of high-stakes divorces.
The Kimberly Guilfoyle Era
Almost immediately after the split, Don Jr. started dating Kimberly Guilfoyle. You probably know her from Fox News or her high-energy speeches at the RNC. They were the ultimate "MAGA power couple" for years.
- They started dating in mid-2018.
- They got engaged on New Year's Eve in 2020.
- They bought a $9.7 million mansion together in Jupiter, Florida.
Most people assumed they were already married because they were always together. But they never actually tied the knot. Despite a four-year engagement, the relationship eventually cooled off. By late 2024, rumors of a split were everywhere after Don Jr. was spotted with a new face in Palm Beach. In early 2025, it became official: Kimberly was heading to Athens to serve as the U.S. Ambassador to Greece, and the engagement was off.
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A New Chapter with Bettina Anderson
So, where does that leave him now? As of late 2025 and heading into 2026, Don Jr. is engaged again. This time it's to Bettina Anderson, a well-known socialite in the Palm Beach scene.
The news broke in a very "Trump" way—President Donald Trump himself announced the engagement during a White House Christmas reception in December 2025. He basically gave the couple his blessing in front of a room full of guests, and Don Jr. took the podium to talk about how happy he was.
Bettina is often described as a perfect fit for the Florida lifestyle Don Jr. has embraced. She’s active in the local social circuit and seems to stay out of the aggressive political fray that Kimberly leaned into. Whether this leads to marriage number two remains to be seen, but for now, they are living together in Palm Beach.
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A Quick Reality Check on the Numbers
People often get confused about Don Jr.’s marriage count because his father has been married three times. It’s easy to let those numbers bleed together. To keep it straight:
- Donald Trump (The Father): 3 Marriages (Ivana, Marla, Melania).
- Donald Trump Jr. (The Son): 1 Marriage (Vanessa).
Why the Public is So Obsessed
It’s not just about the gossip. Don Jr.’s personal life often mirrors the political climate. His divorce from Vanessa happened right as the family was adjusting to life in the White House. His relationship with Kimberly defined the "campaign years." Now, his engagement to Bettina marks a shift toward a more settled, Florida-centric life.
What You Can Take Away From This
If you're following the Trump family history or just curious about the man who might be a future political candidate himself, knowing the facts helps cut through the noise. Don Jr. has had one long-term marriage, one long-term engagement that ended, and is currently headed toward a second marriage.
If you want to stay updated on the specifics of the Trump family tree or their business dealings, it’s best to:
- Verify with primary sources: Check official announcements or reputable biographies rather than social media rumors.
- Distinguish between "partner" and "spouse": In the world of high-profile celebs, people often use these interchangeably, but legally they are very different.
- Watch the real estate: In the Trump world, where someone lives often tells you more about their relationship status than a press release. The sale (or retention) of that $9.7 million Jupiter mansion will be a big indicator of how the final ties with the Guilfoyle era are being cut.
Keep an eye on the social calendars in Palm Beach. That’s where the next chapter of this story—and potentially marriage number two—will actually happen.