Signs Don Jr. Couldn't Handle Kimberly Guilfoyle's Ambition (& That's Why He Dumped Her)

If President Donald Trump has taught us anything, it's that Trump men like to be in control, and it appears the same is true for their romantic relationships. For those still wondering why Kimberly Guilfoyle and Donald Trump Jr. broke up, well, the reason seems to be that Guilfoyle was a tad too ambitious for Don Jr.

It's no secret Guilfoyle loves the spotlight, and she outshone Don Jr. on a few occasions. She threw herself head-first into her beau's father's campaign after she was ousted from Fox News in 2018, and the president's 2024 campaign saw her working hard to elevate Trump once again. Don Jr., meanwhile, has hinted on occasion that he's more of a behind-the-scenes guy, and it stands to reason he'd like to have a partner who is not as boisterous as Guilfoyle. There's also the fact that Jr. has admitted he feels like he's scrutinized for who his father is. "It would be nice not to have people prejudge you because they see your father a certain way and there's no chance you might actually be different," he once told journalist Gwenda Blair (via Politico). He also told Blair that he prefers to have a work-life balance and enjoys taking time off. Guilfoyle, meanwhile, is constantly advocating for Trump's MAGA movement and attending high-profile events, and doesn't show signs of slowing down anytime soon.

It was at Guilfoyle's 2023 birthday party that Jr. quipped she was in charge of their relationship. "I always do what she says," he reportedly told guests, according to a source who spoke to Page Six at the time. It seems that, at some point, Don Jr. decided he was tired of that dynamic, and he moved on with a woman who is the exact opposite of his ex.

Kimberly Guilfoyle's social media posts might hint she's lost without Donald Trump Jr., but it might be safe to say that the latter has found himself. Word on the street is that Jr. and his new girlfriend, Palm Beach socialite and model Bettina Anderson, are gloriously happy, and the fact that Anderson is more laid back than Guilfoyle seems to have a lot to do with it. 

"She can get glammed up and look amazing or go fishing and golfing with him and get sweaty and be laid back," a source told Us Weekly. Alas, Guilfoyle's forced fishy moment with Don Jr. aged as well as their relationship — she clearly wasn't the outdoorsy type — but Anderson seems to fulfill this role just fine. "When it comes to his relationship with Bettina, it's just about them," another source said. "He wants a partner. She doesn't need anything from him and just wants to be with him." 

Before Guilfoyle and Jr.'s 2024 split, there were whispers that members of the Trump family couldn't stand her and that, "She is trying too hard to be in the family" (per Page Six). Additionally, scuttlebutt that Jr. believed his father didn't approve of Guilfoyle has run rampant. Sources told People the eldest Trump son believes Anderson's profession and style will resonate more with his father and that Guilfoyle's fashion and conduct was too brash for the Trumps. "Don Jr. has been telling people for months that Kim is so uptight and always dresses so professionally in these kinds of dresses and high heels, and never looks relaxed or casual," one source claimed. "The tight dresses need to go and she has been told that." Of course, in the end, it wasn't just the dresses that went.