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They say there’s someone for everyone, but even as an optimist (and a hopeless yet realistic romantic), it’s still surprising that anyone would marry Donald Trump Jr. Yet, someone did—Vanessa Trump.
The couple tied the knot in 2005 at Mar-a-Lago (which, honestly, might’ve been the first red flag). Their marriage, however, didn’t last. Now, Vanessa has moved on with Tiger Woods, and Don Jr. has also started fresh, dating Bettina Anderson after ending things with Kimberly Guilfoyle. But what exactly led Vanessa to call it quits?
Money, alleged affairs, and… bacon?
When Vanessa and Don Jr. announced their divorce, they kept things diplomatic, releasing a statement about their commitment to co-parenting their five children. But behind the scenes, sources say the real reasons boiled down to money troubles and infidelity.
According to Page Six, Don Jr. was reportedly “keeping her on a tight budget,” to the point where Vanessa had to ask her mother for financial help. Meanwhile, Us Weekly reported that Don Jr. had an affair with singer Aubrey O’Day during The Celebrity Apprentice Season 5. Vanessa allegedly discovered the affair in 2012 by reading their emails. O’Day has since spoken about the relationship multiple times, including on a 2024 episode of Call Her Daddy.
Even Don Jr.’s mother, Ivana Trump, commented on the scandal, calling the situation “distressing” before casually adding, “I honestly don’t know that many men who can keep their zippers up.” (Yes, she said that about her own son.)
More reasons why Vanessa Trump walked away
Aside from the financial strain and alleged cheating, Vanessa reportedly wasn’t thrilled about Don Jr. frequently posting their kids on social media. She also wasn’t a fan of his constant fishing, hunting, and work-related travel, per Page Six.
Then, there’s the bacon incident. Yes, you read that right. In 2013, Don Jr. tweeted:
“Thought I was having dinner w/ @MrsVanessaTrump till I saw her remove bacon from a sandwich. Who are u & what have u done w my wife?”
Now, is this the worst thing a spouse can do? Probably not. But if someone ate your last piece of bacon, well, that might be worth a discussion.
An unusual beginning and an ongoing Trump connection
Looking back, their relationship may have been doomed from the start. How did they even meet? At an NYC fashion show, where Donald Trump himself introduced them with, “Hi, I’m Donald Trump. I wanted to introduce you to my son, Donald Trump Jr.” If that’s not a fairy tale romance, what is?
Despite their divorce, Vanessa remains connected to the Trump circle. In 2024, her daughter Kai even posted about Elon Musk, calling him “uncle status.” One can only wonder what Grimes would think of that.