Bettina Anderson's Age Gap With Don Jr. Is Painfully Obvious In These Photos
As far as age gaps in political pairings go, Donald Trump Jr. and Bettina Anderson's certainly isn't the most uncomfortable; after all, more than 30 years separates Karoline Leavitt from her husband. The president's son is nine years older than Anderson, the same age gap Don Jr. had with his ex-fiancée, Kimberly Guilfoyle (albeit in reverse). However, he does have a way of dressing himself way older than he actually is — and just like that, what could be a negligible gap looks way worse.
Of course, Don Jr. doesn't need outdated clothes to look much older than Anderson; his graying beard and hair do the work for him. However, the messy T-shirt he wore while engaging in some awkward PDA during the April 2025 LIV Golf tournament made him look seriously slovenly. Other than their cringe-worthy behavior, Anderson looked effortlessly glam and youthful, while Don Jr. kind of reminded us of Steve Carell's character in "The Four Seasons," right down to the sunnies. In case you missed it, that's the one where he has a midlife crisis.
Bettina looks elevated when Don Jr. dresses casual
One of Donald Trump Jr. and Bettina Anderson's first public events together was for an elitist Super Bowl party, so it goes without saying that the event's dress code wasn't exactly black tie. Even so, Anderson pulled up looking equal parts laidback and cool.
On the other hand, Don Jr. looked like a dad who'd dropped his kids off at a party and stuck around for the snacks. Like the LIV Golf tournament, his overly casual outfit only made him look older next to the fashionable Anderson. Why he believed a Henley shirt, chinos, and leather sneakers were appropriate for the VIP red carpet remains to be seen.
They gave peak midlife crisis vibes at Congress
Sticking with the midlife crisis vibes, Donald Trump Jr. took Bettina Anderson to his dad's joint address to Congress in March 2025. This time, both of them were dressed appropriately, but that evidently didn't extend to their behavior — while there, Don Jr. took selfies while Anderson tickled his face.
To be honest, both of them behaved like lovestruck teenagers, but the lack of decorum from what was then a 47-year-old man only made him seem even older than his 30-something date. They were so obnoxious that Ivanka Trump (who has hinted at not being a fan of Anderson) seemingly hushed them.
Bettina looked like a supermodel at an amfAR gala
Not long after they canoodled at Congress, Donald Trump Jr. and Bettina Anderson attended the amfAR Palm Beach Gala together. To say she was a vision would be an understatement.
Clad in a metallic minidress and heels, Anderson gave off young, fun, supermodel vibes. We'll give credit where it's due and say Don Jr. suited up well, too, though his sockless feet awkwardly stood out in try-hard boat shoes. Compared to Anderson, he looked overeager and, frankly, kind of like a dweeb.
The time Don Jr. tried to dress like his cool younger GF
Nothing says "I'm trying to look as hip as my younger girlfriend" quite like copying her outfit, so we probably shouldn't have been surprised when Donald Trump Jr. pulled up to the 2025 FIFA Club World Cup final in July with his sleeves flipped up, mimicking Bettina Anderson. Even so, the cringe factor was undeniable.
Almost more awkward was how difficult it was to tell Anderson apart from Donny's step-mommy, Melania Trump. Granted, Melania's own 'fit seemed lazy by her standards, so it was certainly an off day for the whole family.
Don Jr. and Bettina's age gap was even more obvious in NYC
A few months after their amfAR Gala appearance, Bettina Anderson had another miniskirt moment, and once again, she looked incredible. She could've passed for a 20-something influencer in her bold red outfit, flaunting her great legs at the New York Stock Exchange in July.
Then there was Donald Trump Jr. The president's eldest child looked as though he was borrowing from his dad's bland wardrobe in a navy suit and red tie. Of course, the cosplay extended to the fact that he was hand-in-hand with a much younger woman.
Don Jr.'s protruding pectorals screamed insecurity
Another pic that put Donald Trump Jr.'s age gap with Bettina Anderson on blast was taken on the White House lawn in late July 2025, when the president's son weirdly puffed his chest out to oblivion. He was mocked for his bizarre posture and protruding pectorals on social media, with one person sharing the picture to X and asking, "Is Don Jr. trying to get an American Eagle ad too?"
Don Jr. actually shared the photo and poked fun at himself, and Anderson cheered him on in the comment section. Regardless, the image highlights the insecurity he likely feels about dating a younger woman who many would say is out of his league.
Bettina's bow made her look so much younger than Don Jr.
When Donald Trump Jr. announced that he and Bettina Anderson were engaged in December 2025, he once again went for matching 'fits with his dad. Anderson, on the other hand, donned a chic red column dress with floral detailing and sported a matching bow in her hair. It was young, fresh, and seasonally appropriate — but it was also a reminder that she was a lot younger than her newly betrothed.
Over the years, one thing that all of Don Jr.'s partners have had in common is a love for glam, so it's not surprising that Anderson is a fashion girly. However, if the eldest Trump child doesn't want to be seen as, well, the "eldest" Trump child, it may be time he steps up his game (and not just by copying his fiancée). Anderson has her work cut out for her.