Creepy Karoline Leavitt Moments That Put Her Trump Obsession On Blast

Find someone who looks at you the way Karoline Leavitt looks at Donald Trump. Actually, on second thought ... don't. It's clear that Leavitt's allegiance to Trump knows no bounds. But, every now and then, the press secretary seems to take things too far, and it comes off a bit on the creepy side.

Time and time again, Trump's creepy praise for Leavitt has us side-eyeing their relationship. With closer attention, though, it quickly becomes clear that — against all odds — Leavitt may actually act even weirder about Trump than he does about her. Or, at least, that's how it appears publicly. From countless Instagram posts that highlight Leavitt's over-the-top fixation on her boss to her love of photos of the two of them together (not to mention how lovingly she stares at him), she doesn't hide her apparent Trump obsession as much as we wish she would. And, it's gotten to the point where folks online are calling her out. And, while Trump's former attorney coined her most brutal nickname yet, "Bull**** Barbie," we're starting to think Kreepy Karoline may be the most appropriate nickname of all.

If there was a class called "How to avoid looking creepy 101," one of the first lessons would surely warn against standing in the shadows and staring unblinkingly at someone while they talk. And, this is one of the ways we know that Karoline Leavitt would not pass such a class. In July 2025, Donald Trump spoke to press while on Air Force One. Leavitt was by his side while he spoke — or more accurately, she was standing slightly behind him, staring at the back of his head with a completely blank expression on her face.

Trump: "President Obama was a terrible president. President Biden was the worst president. President Bush... I don't give him high marks either. I give Trump very high marks."

I think Trump is the worst president we've ever had. pic.twitter.com/j1uqFjiQpU

— Ron Smith (@Ronxyz00) July 1, 2025

It seems that, as she often does, Leavitt was there to show her moral support for her boss. The way she was showing that support, however, looked a bit strange and was — unfortunately for her — caught on camera from a particularly jarring angle. With the right background music, this video could be perfect horror movie material.

Karoline Leavitt stirred up controversy in April 2025 when she appeared on content creator Kate Mackz's TikTok account to give a tour of the White House. Mackz earned quite a bit of backlash in the comment section for her choice to use her platform to accept a tour from Leavitt. Beyond that, though, the video had another possibly surprising effect when the comments started to roll in. During the tour, Leavitt showed off her own office, and it revealed just how important Donald Trump was to Leavitt when it came time to decorate her workspace.

Upon entering, Leavitt said, "This is my office. I have, obviously, photos of myself with the president," gesturing to framed photos hanging on her wall. The first photo showed her and Trump, followed by one of her holding her baby and another of her at her first press briefing. Not only did she choose to feature her photo with the president first on the wall, but she also neglected to include a single photo of her husband. So, at least when it comes to her office decor, for Leavitt, it seems that boss status trumps husband status — pun intended.

Karoline Leavitt doesn't just love having photos of her and Donald Trump in her office; she also loves having them on her Instagram — even when it seems a bit odd to do so. Plenty of folks love to share cute photos posing with their partner, their friends, their family members, or their pets on social media. But, how many people post photos on Instagram with their boss just for the heck of it? We have a feeling it isn't many. But, the unusual nature of a post like this did not stop Karoline Leavitt from paying homage to Donald Trump in a simple Insta post that seems much more like something a couple would share. And, the fact that Leavitt seldom posts about her actual husband makes this all the more strange.

In October 2024, Leavitt posted what appeared to be a candid photo of Trump talking to her on Instagram. She captioned it, "The boss." While she was clearly gearing up for Election Day and hoping "the boss" would win and score her the role of White House press secretary, this post still felt a bit too personal.

Interestingly, Karoline Leavitt's candid photo of her with Donald Trump wasn't the first of its kind that she shared on Instagram. On October 1, 2024, she shared a photo of her and Trump walking together from behind, which once again, felt like it would have made more sense if it was her and her husband. Yet, it was the second photo in this carousel that was even more disturbing. In it, Leavitt posed with her then-three-month-old baby in front of a strange portrait of Trump. The portrait showed an ominous-looking Trump pointing straight ahead with the words "Trump 2024" and "In Trump we trust." 

Posing in front of this artwork with her baby definitely highlighted her Trump obsession on its own, but the fact that she dressed her baby in a "Trump for President" onesie made matters far worse. While she bragged in the caption about being "in [her] working mom era," turning your baby into a political prop for a photo op definitely takes "working mom" a bit too far.

As if Karoline Leavitt hadn't already accidentally exposed how Donald Trump-obsessed she really is by showing off her office to the world, another angle made it even clearer. For most people, hanging a photo of yourself posing with your boss in your office would not be an ideal decor choice. Yet, it seems that for Leavitt, this actually wasn't a big enough interior design ode to the president. So, she took the logical next step: adding a tiny cutout of her and Trump on the wall next to her desk. 

The detail was revealed when a photo of her and her baby was posted on X, formerly known as Twitter. Her colleague Margo Martin called Leavitt "Super Mom!" in the caption for working on her computer with her baby in her lap. Yet, it was hard to ignore that little photo on the wall next to her, which seemingly gives Leavitt the ability to catch a glimpse of a photo of her and Trump, no matter where in her office she is sitting. And, despite covering her bulletin board with a few pictures of her baby and an eye-roll-worthy meme, she once again, didn't appear to have any evidence of her husband decorating her desk area. 

In July 2025, Karoline Leavitt posted a photo with Donald Trump that backfired as people side-eyed their cozy relationship. And, this basically proved that lots of people think her Trump obsession has gone too far. The Instagram photo carousel in question included pics of Leavitt's trip to Scotland. Unsurprisingly, though, the first photo was one of her and Trump on the golf course. At this point, we're used to seeing Leavitt post about Trump on social media the way a high schooler might post about their new boyfriend. Yet, on this post in particular, folks didn't hold back in the comment section.

"Looks like you like him more than Melania" one Instagram-user commented on the post. "You look just like Monica Lewinsky adoringly did!" said another. One called Leavitt and Trump "The couple from hell" with a vomiting emoji. Evidently, Leavitt has officially shared one too many couple-y looking photos with Trump for netizens' taste. And, we have a feeling that she's just getting started.