Bettina Anderson's Bad Habit Won't Earn Her Any Brownie Points With Trump (Sorry, Don Jr.)

Donald Trump Jr.'s relationship with Bettina Anderson has been pretty complicated thus far. The eldest son of President Donald Trump began romancing the model and socialite while he was still technically engaged to Kimberly Guilfoyle. But, once the tabloids caught them getting cozy, Don Jr. gradually dropped the pretense that he was still planning to get married. By Christmas 2024, Anderson was a welcome guest at Mar-a-Lago, and she began posting coy photos of floral gifts, beach trips, hunting outings, and other sweet memories. The Palm Beach local even spent spring break 2025 with Don Jr. and his four younger kids, a further indication that this is more than just a fun fling. In fact, Don Jr.'s girlfriend is even reportedly waiting for a marriage proposal of her own, with insiders claiming she doesn't want to drag things out too long without a firm commitment. 

Here's the catch, though; a future proposal will likely hinge on the approval of Anderson's prospective father-in-law — and her own bad habit may get in the way of it. In the undated photo seen below, Anderson was caught in a candid moment, wearing casual clothes and holding a cigarette. She has used cigarettes as props in modeling shoots before, but this pic indicates that she actually does smoke. If so, that won't sit well with the president who, from the time his five children were old enough to understand, strongly warned them against adopting common vices. "I have smart children. They've been good academically [...] I would always tell them no drugs, no alcohol, no cigarettes," he explained to the Detroit Economic Club in October 2024 (via YouTube). With such a hardline view, it's possible that Donald could discourage his son from marrying a smoker.

A sad truth of parenthood is that your kids don't always follow the wise advice you dispense and, clearly, the president is no exception. Having seen what alcoholism did to his beloved older brother Fred Trump Jr., Donald Trump urged his children to follow his lead and never drink or smoke. But the temptation of booze-filled frat parties was too much for his eldest son to resist. In his wild college days, Donald Trump Jr. earned the brutal nickname "Diaper Don" because of his reputation for drinking to the point of losing bladder control. He now claims to be longtime sober, but both his ex-fiancée Kimberly Guilfoyle and current flame Bettina Anderson are known party girls, and it appears that the latter also indulges in smoking which, notably, none of the Trump children do. 

Thus far, Anderson's vices haven't got in the way of her romance with Don Jr. That might soon change, though, if the happy couple decides to take it to the next level. The president is extremely image-conscious, and he prefers to be surrounded by people who make him and his family look good. Donald always mentions measurable qualities like intelligence and success (and Barron Trump's height, of course) when discussing his children and their spouses, rather than their love or compassion for others. Don Jr.'s attempt to win his dad's approval for his new girlfriend reportedly got off to a bad start because of Anderson's history of expressing more liberal views. The model and socialite is trying to change that image by adding more MAGA messaging to her social media, but she may need to kick the cigs as well if she wants to stay in proximity to the White House.