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Uh-Oh: Looks Like There Might Be Trouble in Paradise for Don Jr. and Kimberly Guilfoyle

Is this it for the former First Son and his washed-up fiancée?

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Donald Trump Jr. has “moved on” from his longtime sweetheart Kimberly Guilfoyle, says one prominent Republican. Rick Wilson, a former strategist for the GOP and one of the founders of the Lincoln Project, shared a viral clip of Kimberly’s speech at a “victory dinner” for Florida Republicans. He captioned it “She’s looking rough since Don Jr. moved on.”

The clip was a video montage we reported on earlier, in which she can be seen desperately begging the audience to give her some kind of reaction to what she was saying.

Then Rick Wilson, who knows what he’s talking about, added:

Guilfoyle had spouted off some inspirational nonsense that lulled the crowd full into a hush, spoiling the climax of her speech with tormented silence.

“I’m here to tell you don’t lose hope. On a personal note, I can tell you that I am as hopeful as ever. Because Americans from all walks of life have had enough of the Democrats’ decline,” she said to the audience. “And we are ready, we are willing, and we are able to spark a new era of American exceptionalism.”

No response.

Now, that could be because nobody wanted their voice to stand out in the crowd after such a cringe-worthy line — American exceptionalism? Really? — but it’s more likely that she was just in spectacularly bad form that night.

“You can clap for that,” she meekly suggested. A few even did after she prompted them.

There were rumors of Don Jr. and Kimberly’s breakup a little over a month ago, but friends assured the world that the ever-wired mini-Trump and his surgery-gone-wrong girlfriend were still going strong.

But they certainly haven’t been together lately. The closest they’ve come to each other publicly is when Kimberly tags Jr. in the delightfully bad cooking videos she likes to post on Instagram. You know, where she puts on a $400 dress and some high heels and makes chicken with her nearly waist-length hair dangling over the food. Nara Smith she is not.

They haven’t even appeared in the same social media uploads together in a month. And these two have been dating since 2018, and engaged since 2020…that’s a long time to stay engaged.

The thing is, it might not be her breaking up with him. He might just be annoyed by how… Well, annoying she is. Her support of his dad can only be described as “relentless,” which is great for a campaign but terrible for a relationship. Who wants to date a MAGA weirdo, am I right?

But the way she talks is just a little too on the nose for someone who is not themselves a politician.

“None of those people, those fake Republicans, RINOs, I’ll throw the RNC in there with that, all these people have to go. They’re not gonna be part of our team. They suck!” she said at a campaign event back in December. “We’re not gonna reward them. They’re traitorous, they’re disloyal and they’re unqualified! So that’s it, I’ve had enough with all those people.”

What have you had enough with? Being invited to their dinner parties? Being a name people remember?

Whatever the status of Kim and Junior’s relationship is, I wish them both the future that they deserve.

Andrew Simpson
meet the author

Andrew is a dark blue speck in deep red Central Washington, writing with the conviction of 18 years at the keyboard and too much politics to even stand. When not furiously stabbing the keys on breaking news stories, he writes poetry, prose, essays, haiku, lectures, stories for grief therapy, wedding ceremonies, detailed instructions on making doughnuts from canned biscuit dough (more sugar than cinnamon — duh), and equations to determine the airspeed velocity of an unladen swallow. A girlfriend, a dog, two cats, and two birds round out the equation, and in his spare time, Drewbear likes to imagine what it must be like to have spare time.

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