Kimberly Guilfoyle's Family News Proves She's Not Done With Don Jr. Just Yet (Sorry, Kai)

A child's acceptance to the college of their choice is always an exciting occasion, and normally it's a drama-free one, too. But when the Trump family is involved — well, that's a different story. On March 14, 2025, Kimberly Guilfoyle posted such an announcement to her Instagram Stories. It showed Guilfoyle's son Ronan Anthony Villency standing in front of a cake decorated with the University of Miami's logo and school colors. "Congratulations Ronan!" she wrote. "We are so proud of you. Lets [sic] go Canes!" 

Here comes the grab-your-popcorn part. Seven months earlier, Kai Trump also shared her college news on Insta. "I am beyond excited to announce my verbal acceptance to the University of Miami," she gushed. "I would like to thank my mom, Vanessa, and my dad, Don, for always supporting me through my journey." That dad, of course, is Donald Trump Jr., who ditched Guilfoyle in the most humiliating way after six years together by leaving her for his mistress. He brought Bettina Anderson to major Mar-a-Lago events at holiday time, signifying the relationship was official. (Don Jr. had to make sure his father, President Donald Trump, approved of the new lady love.) Since then, Anderson has been happily posting coy pics of floral gifts, weekend hunting jaunts, and a romantic island getaway, while Guilfoyle bravely continues to offer overflowing messages of praise for the man she hoped would be her father-in-law. 

So the president's son and his ex-fiancé have children bound for the same college. Throw a new girlfriend into the mix, and you've got the makings of a classic sitcom! (Might we suggest the title "Raising 'Canes"?)

If Kai Trump hoped to escape her dad's fraught romantic life by moving to college, Kimberly Guilfoyle's news just shattered those hopes. Ronan Villency, who might have been her stepbrother, is also going to the University of Miami, so Kai will still have a connection to both him and his mom for the next four years. While Guilfoyle and Donald Trump Jr. have been keeping their split Bennifer-civil, insiders have hinted the former Fox News host is quietly seething. When you've been planning a future of White House galas and hoping for the cachet that comes from being wed to a first son, it's got to be devastating to watch another woman suddenly take that place. 

There are so many questions surrounding the whole awkward situ. Were Don Jr. and Guilfoyle still together when they discussed college choices with their teens? Was it their plan to have Kai and Ronan at the same school, and do they have any regrets now? How often will the kids actually see each other? UM has more than 19,000 students, so it would be pretty easy for them to avoid each other if they wanted. Plus, we don't know yet whether they'll be taking the same classes, and Kai will be busy much of the time with her guaranteed spot on the acclaimed women's golf team. Will the ex-couple continue to show a united front at their children's sporting events, and will Don Jr. dare to bring new girlfriend Bettina Anderson along? Most of all, what do Ronan and Kai think about everything that's transpired over the last year? 

Only time will tell how this will all play out, but we predict some Hurricanes ahead — both in and out of the university.