Don Jr.’s New Girlfriend Won Over Kai & Vanessa Trump Faster Than Kimberly Guilfoyle Ever Did – The List
The hits just keep coming for Kimberly Guilfoyle. While the former prosecutor clearly hasn’t moved on from her relationship with Donald Trump Jr., he (and his family) certainly have — and it’s clear they like Bettina Anderson more than her. From going on a spearfishing spring break excursion with four of Don Jr.’s kids to watching the 2025 Super Bowl looking like a big ol’ happy family, Anderson has easily become part of Don Jr.’s world.
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The first son has five children with ex Vanessa Trump. Though rumors first began swirling that he was seeing his new “friend,” socialite Anderson, in September 2024 — while Don Jr. was still dating Guilfoyle — the duo didn’t go public with their relationship until that December. However, around that same time in fall 2024, a couple of photos and one video were posted to Instagram by House Inhabit writer Jessica Reed Kraus that show Anderson cozying up to Vanessa and daughter Kai Trump around a fire.
“Don Jr. surprised a meetup hosted for my followers in Jupiter, Florida, showing up with his daughter and ex-wife, Vanessa,” Kraus captioned. The post gave a clear indication that Vanessa and Kai, especially the former, were fully comfortable with Anderson’s presence. Unfortunately for Guilfoyle, that never happened when she was part of the family.
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Many people thought Kimberly Guilfoyle and Kai Trump didn’t get along
It’s not like Kimberly Guilfoyle didn’t try, but considering that she got together with Donald Trump Jr. the same year his marriage to Vanessa Trump ended, it’s not surprising they didn’t all sing Kumbaya and become besties. For starters, there were signs Guilfoyle didn’t get along with Kai Trump, one being that Donald Trump’s oldest granddaughter doesn’t even follow the appointed U.S. Ambassador to Greece on Instagram. In fact, Guilfoyle tried staying in Kai’s good graces in March 2025 by commenting emojis on one of Kai’s Instagram carousels. But not only did that fail miserably for her, Bettina Anderson had already beaten her to the punch by writing her own emojis on the social media post.
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The news personality needs to leave her good memories with Don Jr. in the past and go make new memories with someone else. Maybe her next relationship won’t be nearly as drama-filled as this one was.
