20 most cringeworthy snapshots of Donald Trump hanging out with women


The Smile of Someone Who Just Wants to Vanish

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While this was meant to be a light-hearted photo op with Paula Zahn being kissed by both Richard Cohen and Donald Trump, the image takes on a creepy undertone because it appears as though she simply wishes to fade into the background and vanish.

Gotta Have Faith

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In this shot from the Fifth Annual Gourmet Gala March of Dimes Benefit in 1992, Donald Trump plants a kiss on Faith Daniels. However, in a rare moment of introspection, Trump’s expression seems to betray a sense of questioning, as if he’s pondering the direction of his life.

Feeding Barbara Walters

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While the idea of “Trump handing a woman a snack” might not sound inherently creepy, the image of him hand-feeding Barbara Walters like she’s a baby bird is one that’s bound to linger in your mind long after you’ve seen it.

Creeping Out Katie Couric

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Credit where it’s due: Katie Couric is a seasoned entertainment professional. That’s evident in how she maintained her composure when faced with Trump’s grab at the Entertainment Industry Foundation’s Colon Cancer Benefit back in 2004.

Strike A Pose

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In these two sets of photos, Trump strikes poses with his then-girlfriend Kylie Bax and later with Miss New York and Miss Connecticut. While the women offer genuine smiles, Trump attempts to exude a suave playboy vibe but ends up resembling Patrick Bateman cruising around in his limo.

Professional Creep?

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At the Playboy Magazine 40th Anniversary Press Party in 1993, Trump appears to have stumbled upon a revelation. By focusing solely on photographing the beautiful women around him, all the intense staring seems slightly less creepy—at least in his mind.