The Smile of Someone Who Just Wants to Vanish
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
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
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
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
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?
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.