20 Most Awkward Photos of Donald Trump With Women

All presidents end up being controversial in their own way. But at this point, it’s fair to say that Donald Trump is the most controversial living president.

There are many things he said and did in his four years as president that could be considered controversial. But one of the biggest sources of controversy occurred before he was elected: his general creepiness around women!

This became public knowledge when audio leaked from Trump speaking to Access Hollywood. There, he told Billy Bush that he liked to kiss women and grab them by their private parts without their consent. Pretty soon, outlets like Rolling Stone were exposing Trump’s creepiness around women, including Trump’s penchant for walking in on Miss Teen USA contestants while they were changing clothes (some of these girls were only 15 years old).

These bombshell revelations changed how we viewed all those old photos of Trump hanging out with different women. And we’ve rounded up the absolute creepiest photos of Donald Trump with women.

Trump and the teens

Trump strikes a pose with contestants at the Miss USA and Miss Teen USA Pageants Press Conference in 1999. These women look like they want to die, but at least Trump’s not watching them change clothes!

Getting the “evil eye” from Melania

We don’t always get to see others reacting to Trump’s creepiness. But here, Melania Trump (back when she was just Melania Knauss) looks weirded out that Trump is kissing Jennifer C. from The Apprentice.

Leering at another woman

At some point, just about everyone learns that it’s rude to stare at other people. Trump obviously never got that memo and is happy to downright leer at Sports Illustrated model Roshumba Williams, even though his then-wife Marla Maples is standing right next to him!

Is this a lost episode of ‘Will & Grace’?

Back in 2005, Trump was more celebrity than a politician, and he appeared at the 57th Annual Emmy Awards performing with Megan Mullally. It was meant to all be in good fun, but Trump 100% looks like a villain from a bad episode of Will & Grace.

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What’s with that face?

This photo of Trump clutching both Melania and 1997 Playmate of the Year Victoria Silvstedt would have been creepy no matter what. But Trump looking like he is literally sucking all of the air out of the room makes it downright strange.

Kissing Miss Universe

In another universe, this photo of Trump kissing Miss Universe Alicia Machado might have been kind of cute. But thanks to Trump’s own words, he enjoys doing this whether women want it or not, which really ups the creep factor of the photo.

Face to face with Heidi Klum

Back in 2008, Trump was in a good mood: he was celebrating the unveiling of the Trump International Hotel & Tower Dubai. This presumably caused him to kiss Heidi Klum, but this photo makes it look like he is more interested in nibbling on her cheek.

Unwanted kiss

Is there any other photo that better encapsulates the creepiness of Trump towards women? Here, Miss Universe 2012 Olivia Culpo is trying to pose for a photo, but Trump looks like he wants to suck the diamonds right out of her crown.

Freaking out Pamela Anderson

Pamela Anderson was kind enough to show up and add a little star power to the “Donald J. Trump Birthday Quarter Million Dollar Giveaway” in 2005. Chances are that she didn’t know he would try to suck her soul out through her face!

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More like Ivanka “Rump”

Trump has made no secret of the fact that Ivanka is his favorite kid, and he once told the audience of The View that he might be dating her if they weren’t related. Oh, and he once agreed with Howard Stern that Ivanka was “a piece of ass.”

That context is important because it makes Trump reaching for her butt look that much creepier. And let’s face it: this image was pretty damn creepy to begin with.

Images just dripping with “creepy”

Trump has a long history of thinking the Miss Universe contestants care about him or desire his affection. This image captures the moments where two contestants (Stefania Fernandez and Tara Conner) absolutely scream “please back up” to a man who neither understands nor cares.

Meeting a Playboy Bunny

Shocking nobody, Donald Trump liked to hang around with Playboy models and at Playboy events. But judging from the withering look of this Playboy Bunny at the Betsey Johnson Spring 2001 Fashion Show, some of these women really didn’t want his attention!

Looking kind of paranoid

Normally, one of Trump’s best/worst qualities is that he is completely shameless. But this photo captures the exact moment he seems to wonder whether he should really make out with Melania while people are snapping pics.

Ivanka in his lap

This image has so many weird things in it. First, there’s the weirdness of a teenage Ivanka sitting in her father’s lap. But the best part is the man on the far right who seems just as freaked out as the rest of us are by this display!

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The smile of a woman who wants to just disappear

This was staged as a fun photo with Paula Zahn getting kissed by both Richard Cohen and Donald Trump. But the photo is creepy in part because it looks like she wants to just sink into the earth and disappear.

Gotta have Faith

Here, Donald Trump is kissing Faith Daniels at the Fifth Annual Gourmet Gala March of Dimes Benefit in 1992. In a rare bit of introspection, Trump looks like he is wondering what the hell he is doing with his life.

Feeding Barbara Walters

On paper, “Trump hands a woman a snack” doesn’t sound that creepy. But this image of him hand-feeding Barbara Walters like she is a baby bird is guaranteed to haunt your brain cells forever.

Creeping out Katie Couric

We have to hand it to Katie Couric: she is a true entertainment professional. And that’s how she kept her composure in the face of Trump grabbing her at the Entertainment Industry Foundation’s Colon Cancer Benefit back in 2004.

Strike a pose

Here, we have two different Trump pics: one where he poses with his then-girlfriend Kylie Bax and another where he poses with Miss New York and Miss Connecticut. In both sets of photos, the women offer normal smiles. Meanwhile, Trump tries to look a dashing playboy and comes across like Patrick Bateman cruising around in his limo.

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Professional creep?

At this Playboy Magazine 40th Anniversary Press Party in 1993, Trump has seemingly discovered a secret. If you just take pictures of the beautiful women, all of the staring involved looks marginally less creepy.