Is Kimberly Guilfoyle Dating Again? Signs She's Ready For New Love After Don Jr. Breakup

Since Kimberly Guilfoyle and Donald Trump Jr. called it quits in late 2024, in a split that was likely way messier than it seemed, the political pundit and ex-wife of California Governor Gavin Newsom has seemingly been a bit adrift. She's tried her hand at being an influencer, but her recent social media posts have hinted that she's somewhat lost without Don Jr. However, that seemingly hasn't kept her from dipping her toes back into the dating pool and looking for love again.

As far back as February 2025, Guilfoyle teased that she had a romantic suitor when she posted a snapshot to her Instagram story showing off a bouquet of red roses, tied together with a crimson bow. However, she never revealed exactly who the roses were from (and of course no one has suggested that she sent those flowers to herself in response to Don Jr.'s rebound romance with model and socialite Bettina Anderson).

Back in December 2024, just a few days before Don Jr. officially confirmed his split from Guilfoyle after months of speculation, a source told Us Weekly that Guilfoyle was actively dating and looking for love. She didn't do much to hide that fact either, considering the slew of insanely leggy looks Guilfoyle rocked in the months after their breakup. Despite Don Jr. and Anderson seemingly trying to rub their romance in Guilfoyle's face with their PDA and social media posts, Guilfoyle isn't letting it keep her down.

Kimberly Guilfoyle and Donald Trump Jr. got engaged in 2020, two years after they began dating in 2018. Their romance lasted until 2024. Rumors began swirling that Don Jr. had been stepping out with model Bettina Anderson while still very much engaged to Guilfoyle, and their low-key affair may have even been going on for several months before Don Jr. finally called things off. A source told People in December 2024 that Guilfoyle knew about the affair, but let it slide. "For the most part Kim has looked the other way because she loves the power and lifestyle," the source told the outlet.

Things haven't appeared to be easy for Guilfoyle since their split either. She reportedly briefly reconnected with Governor Gavin Newsom when it came to booking a guest on his podcast back in March 2025, and she's been posting a whole lot of sad social media content as she navigates the murky waters of partial fame and trying to remain politically relevant on the outskirts of a divisive administration.

Meanwhile, Guilfoyle's ex has been laying it on really thick when it comes to showing off his new romance on social media. They spent the 4th of July weekend on a trip to Aspen together, often share PDA at major political galas, and have generally done everything to hammer home the fact that Don Jr. has fully moved on from Guilfoyle.