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Since Donald Trump Jr. and Vanessa Trump ended their marriage seven years ago, Don Jr.’s romantic endeavors have remained under public scrutiny. During most of that time, he was engaged to Kimberly Guilfoyle, a former Fox News personality and the current ambassador to Greece, with whom he recently separated in a rather dramatic way. (Rather than an official breakup announcement, Jr. simply appeared with a new partner, socialite Bettina Anderson, leaving Guilfoyle in a state of surprise and prompting speculation about her ambassadorship.) Meanwhile, Vanessa remained relatively out of the public eye—until recently, when it was revealed she’s now dating Tiger Woods.
Yes, that Tiger Woods, who has had quite an eventful week, also announcing he’s recovering from surgery for a ruptured Achilles tendon, all while Barack and Michelle Obama are reportedly working on a biopic about his life. Perhaps it’s time for a third-act revision to include Vanessa! The Daily Mail noted that they’ve been dating since Thanksgiving. It’s uncertain how they crossed paths, but Vanessa, 47, has a strong connection to golf through her and Don Jr.’s eldest daughter, 17-year-old Kai, who excels in the sport. According to Page Six, Kai attends the same school as Woods’ two teenage kids. Woods, 49, is also longtime acquaintances with President Donald Trump; they played golf together just last month, and Woods was honored at a White House Black History Month event. (It appears DEI is acceptable as long as it involves golf.)
Although one might assume that Don Jr. could feel insecure knowing his ex has moved on with one of the most renowned athletes globally, all we know about his reaction to this news is from an “insider” who told People that he is “cool” with it. He tends to be quite level-headed, so this seems plausible. Vanessa and Don Jr. were married for 12 years and share five children; their relationship faced allegations of infidelity and financial issues. During their divorce proceedings, tabloids suggested that Vanessa filed for divorce after receiving a substantial inheritance due to her father’s investment in Rao’s Specialty Foods, which provided her what People labeled a “marinara-sauce windfall.” (As if further proof was required that Don Jr. lacks flavor.) Since their separation, the two have maintained a cordial relationship, with Vanessa attending President Donald Trump’s second inauguration this year alongside Don Jr.’s new girlfriend Anderson, who is reportedly a former friend of hers.
Although it has been some time, many may remember that besides being hailed as one of the greatest golfers ever, Tiger Woods is also infamous for his infidelities. The exposé of his extramarital affairs during his marriage to Swedish model Elin Nordegren, the mother of his two children, made headlines in 2009. His romantic history has mellowed somewhat since, although there was an issue involving an ex-girlfriend and a nondisclosure agreement a few years back. Still, one can understand why some women might hesitate before getting into a new relationship with him. Before Don Jr., Vanessa was linked to various high-profile figures, including an accused member of the Latin Kings gang, a Saudi prince, and Leonardo DiCaprio. So perhaps the warning signals are just overlooked by her.
In the end, what should we make of this new couple? Is it a win that it’s likely causing Don Jr. some distress, or is it troubling that another public figure is becoming further entwined with Trumpworld? Honestly, it’s probably a mix of both. A part of me, of course, is curious about how Trump himself feels about this news. It takes quite a bit for me to show interest in golf, so hats off to everyone involved for that.
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