Donald Trump Flirts With Fox News Anchor Dana Perino On Air (& She Looks So Over It)

During an appearance on Fox News, Donald Trump tried to work his charm on Dana Perino, but she didn't appear to want any part of it. POTUS didn't seem to mind that rumors floated around Perino's alleged plastic surgery and Botox use, as he gushed over her while teleconferencing in on an episode of "The Five" on March 26. Perino had questions about how people in Iran were coping amid the conflict, but Trump had little interest in discussing the matter. Instead, he deflected the question by reminiscing about his longstanding relationship with the Fox News anchor. "But first, do you remember when we had lunch years ago in the base of Trump Tower when it was a brand new building?" he replied to Perino. 

Then he decided to seemingly shoot his shot live on-air and attempted to flirt with "The Five" host. "You haven't changed. Now I'm not allowed to say this, it's the end of my political career, but you may be even better looking [now]," Trump added. The other hosts responded with laughter. In an attempt to downplay the flirtatious comment, Perino said Trump should see how she looks without makeup. "Fox hair and makeup has a lot to do with that," she responded to Trump, while trying to refocus the questioning.

"Do you have any insight into how the Iranian people are doing? Do they have drinking water? Food?"

TRUMP: "Remember when we had lunch? You may be even better looking now." pic.twitter.com/IT40BaatEH

— The Tennessee Holler (@TheTNHoller) March 26, 2026

The line about Perino's beauty not only made her uncomfortable, but some viewers as well. "The married President of the United States just made a pass live on FoxNews," one X user wrote. Others believed the Commander-in-Chief was employing a specific tactic by mentioning Perino's appearance. "Classic Trump distraction technique [laughing emoji] Question about basic needs, answer about looks," another wrote. That was not the first time Trump focused on the attractiveness of a reporter or made reference to how inappropriate the topic was to discuss.

While signing a peace deal between the Democratic Republic of Congo and Rwanda at the White House in June 2025, Donald Trump zeroed-in on reporter Hariana Verás. Verás is the first African-born journalist to be accredited by the White House, and she was introduced by Karoline Leavitt at the peace signing. POTUS decided to heap praise on the reporter. "This is politically incorrect, she said 'she's beautiful,' and you are beautiful," he said to Verás (via X). 

Trump then used the same technique to minimize his comment as he used when speaking to Dana Perino on Fox News. "I'm not allowed to say that, you know, that could be the end of my political career," he said. Then Trump made a half-hearted attempt to show he cared about more than just Verás' attractiveness. "But you are beautiful, and you're beautiful inside. I wish I had more reporters like you," he added.

Later that year, as chatter floated around Pam Bondi having undergone plastic surgery, Trump once again joked that talking about a woman's beauty would land him in hot water. Speaking during a cabinet meeting in August 2025, Trump bashed Chuck Schumer for looking as if "he's aged 100 years," and then seemed to catch himself for possibly crossing the line. "And I don't like getting into looks. When you're in politics, looks don't matter," Trump said in a video shared on X before making a bewildering pivot, speaking about Bondi's attractiveness. "I look at Pam, I would never say she's beautiful because that would be the end of my political career," Trump said, using the same half-joking refrain that always garnered laughs from the crowd.