Cozy Trump & Karoline Leavitt Pics That Will Keep The Rumor Mill Going

Between President Donald Trump going gaga for Karoline Leavitt's lips (deep breaths, people, we're starting strong!) and the White House press secretary's eyes quite literally lighting up whenever her boss talks, it's not exactly surprising that affair rumors about Trump and Leavitt have long been doing the rounds. Of course, that could just be gossip, but we don't doubt that the duo would be absolutely thrilled to see just how giggly they appear around one another in pics. 

Andrew Harnik/Getty

We'll kick things off with the moment the divisive politician proudly introduced one of Trump's 10 grandchildren to the press pool onboard Air Force One, and Leavitt almost looked as though she was jumping at the opportunity to play happy families with him. Granted, she may just have thought it was funny seeing the youngster being interviewed and photographed at the exact same time she laughed about it, but there's no question it looked like Leavitt was "in" with the fam. 

Air travel can be stressful, and that's without a crowd of reporters gathering around to eagerly ask questions, Secret Service agents holding court, and high-profile passengers to keep safe. But don't worry, as long as the youngest White House press secretary in history has the boss in her sights, she's chipper. At least, that's the impression we got when Karoline Leavitt was photographed gazing on happily while President Donald Trump spoke with the media onboard Air Force One. We've all got our coping mechanisms, right? Granted, we don't all work for people whom we seemingly idol worship, but that's besides the point. 

It's one thing to get on well with your boss. It's quite another to be so enamored as to gaze up at him adoringly as he enters a room, as though he brought the sunshine in with him. Unfortunately for Karoline Leavitt, she did just that when President Donald Trump made an appearance at a January 2026 White House press briefing, and the embarrassing moment got caught on camera. If he had said something particularly awe-inspiring when Leavitt was captured beaming up at him, we might have been able to look past it. However, what Trump actually said was, "Wow. That's a big crowd," (via YouTube). But clearly it was still heart-eyes worthy to her.

Okay, strictly speaking, the White House press secretary did want us to see the cozy snap of Karoline Leavitt and President Donald Trump on his golf course during a trip to Scotland. After all, she posted it on her Instagram account. However, what the White House staffer probably would have liked to avoid were the intensified rumors that Leavitt and Trump were having an affair, after they shared a golf cart. Unfortunately, the pic of them looking super close wasn't exactly giving "professional relationship" so much as raising eyebrows. Then again, one might argue they resembled a father and daughter duo rather than a couple, so there's always that.

Another pic that Karoline Leavitt chose to share on Instagram, but likely without thinking it might backfire, was one she posted with President Donald Trump on New Year's Day 2024. The two got super close for the snap (significantly more so than in earlier pics of them together), prompting at least one Instagram user to snipe, "Probably preparing her to be his next wife!" Yikes. Something tells us the same critic likely had a field day when the White House staffer began dressing more like the former model (something that prompted haters to call Leavitt a Melania wannabe).

When Karoline Leavitt announced that she would be Donald Trump's national press secretary for his 2024 presidential campaign, she chose a surprisingly cozy pic of the duo. The controversial politician has his hand on her shoulder — and we seriously hope she just didn't realize how it would look. Unfortunately for Leavitt, plenty of social media users did. Several netizens argued that it was inappropriate for a work environment, for instance. For what it's worth, Leavitt doesn't seem to have been bothered by comments along those lines. After all, she never deleted them. 

A pic of a boss with his hand on a subordinate's shoulder is eyebrow-raising enough, but consider this shot of President Donald Trump with his hand not just on subordinate Karoline Leavitt's shoulder, but grazing her hair, too (Side note: Now we know where Erika Kirk found inspo for her shady hug with JD Vance). We're not sure why Leavitt would choose to include it in an Instagram carousel, but perhaps she was desperate to share a snap with the boss and just didn't have many to work with. Still, the proud Trump staffer did include it as the photo dump's third slide, so maybe even she knew it was inappropriate. We live in hope!