Don Jr. Takes Bettina Relationship To Next Level (& We Have Kimberly Guilfoyle Deja Vu)
Donald Trump Jr. and Bettina Anderson may have initially kept their relationship on the down low (since he was apparently still engaged to Kimberly Guilfoyle at the time) but they have fully embraced it now. The couple is even involving Don Jr.'s five kids with Vanessa Trump. Although Don Jr.'s inner circle reportedly isn't happy about his romance with Anderson, his children seem to have given it their seal of approval.
The Florida socialite reposted a photo from Don Jr.'s Instagram to her Stories that showed her fishing with her man and three of his kids: Tristan, Spencer, and Chloe Trump. The businessman's eldest son, Donald John Trump III, was also present at the hangout, but daughter Kai Trump appeared to be absent. While Anderson didn't add a caption to the pic, Don Jr. wrote next to his simply: "Spring break spearfishing crush fest with the little (and not so little) people." It was a carousel of pics, but that was the only one featuring his girlfriend; the rest were of Don Jr. happily mucking about with his kids.
If this fishing outing seems familiar, it's probably because Don Jr. did the exact same thing with Kimberly Guilfoyle back in June 2018. The only real difference is that they went sans children. The businessman became Instagram official with Guilfoyle after posting a photo of the couple with Brett Michaels, the lead singer of glam rock band Poison. Two days later, he shared the fishing trip pics. Now that Don Jr. is going fishing with his new squeeze — and took his kiddos along for the fun — that has to sting for his former fiancée.
Kimberly Guilfoyle is still trying to maintain a connection to Don Jr.
This fishing expedition is yet another entry in the growing list of times that Donald Trump Jr. and Bettina Anderson have rubbed their romance in Kimberly Guilfoyle's face. Whether it involves flirty PDA or lavish Valentine's Day plans, Don Jr. and Anderson seem to thrive on showing off their love — and, heartbreakingly, the TV personality can't seem to let her past relationship go. While the former Fox News host may act like she is enjoying her new single era, Trump insiders hinted that Guilfoyle hasn't been handling the Don Jr. split as well as it seems on the outside.
She's also struggling to stay relevant in his life by any means necessary — including through his kids. In March 2025, the U.S. ambassador to Greece commented on Kai Trump's Instagram carousel with a slew of emojis, but unfortunately Anderson had already beaten her to it. By doing likewise, it made Guilfoyle look slightly desperate in comparison. Regardless, Don Jr. has clearly moved on from her. Taking your girlfriend on a fishing trip with your kids feels like a big step for a relationship, especially since the children seemed totally comfortable with Anderson being there.