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Katy Perry’s 15 Most Awkward Photos

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Katy Perry’s 15 Most Awkward Photos


Katy Perry is someone who, for better or for worse, is in our pop culture consciousness now. From the day she came into our frame of view with “I Kissed A Girl (And I Liked It)” (altogether now: the taste of her cherry Chapstick!), the singer — who, interestingly enough, was born Kate Hudson (now that would have been confusing!) — Perry is someone we adore because she seems like she’s one of us.

And the reason we think she’s one of us is because she takes doofy pictures from time to time.

And what’s great about the singer is that she doesn’t hold off on her doofiness when she’s with fans; some of her doofiest photos are with fans (we’ve got a few for you coming up). Then again, if you had to grow up in an ultra-conservative household — where you couldn’t refer to a “lucky” breakfast cereal for fear that you would conjure up Lucifer, and “devilled eggs” had to get renamed “angel’s eggs” — you’d be a little weird around people too.

Here’s our list of Katy Perry’s seriously awesome, but seriously awkward photos.

15. She Kissed A Girl, But We Don’t Think She Liked It

Katy Perry and her Awkward Fan Photos

Things have been known to get a little nutty at Rock in Rio — trust us, we’ve been there — but in 2015, Katy Perry got to experience it firsthand. That’s where this — one of Katy Perry’s most awkward fan photos — comes from: according to Rolling Stone, who was there to know, the fan in question had a bit too much of the plonk (which is bound to happen when you’re at an outdoor festival in Brazil; it’s almost called for). So, when Katy Perry invited her onstage, she got a bit too happy that she was there, and ended up kissing her on the neck — while, of course, snapping a selfie of the act for all of posterity to bear witness. But Perry was a trooper about it, and laughed it off — even though this photo looks quite a bit awkward. For what it’s worth, the fan — who was named Rayane — posted the pic with the pop star on Twitter, following it up with another photo and a shout-out: “Thank you bb, I love u so much #ROCKINRIO.”

14. When You Literally Have To Kiss Katy Perry’s A**

Katy Perry Perez Hilton Awkward Fan Photos

Yes, this is a photo of blogging provocateur Perez Hilton kissing Katy Perry’s a** at the MTV Europe Awards in 2015. There are so many things about this shot that make it one of the biggest awkward photos on this list — the literal a** kissing notwithstanding, let’s talk about Perez’s choice of fashion. Crocs? A sweater vest? Little Lord Fauntleroy pants? This is just a hot mess — and certainly not one of Perez’s finer fashion choices, which is unusual, because he’s quite the snappy dresser. And as for Katy Perry — it’s not that she looks bad. In fact, it seems that she coordinated the dress to match the confetti. But those shoes — good Lord, Katy, those shoes are just terrible. Then again, the MTV Awards are known for being the less “serious” sister of the more grown-up shows, so perhaps they were just fitting right in.

13. The Awkward Fan Photos Hall Of Fame

Katy Perry Awkward Fan Photos Hall of Fame

There are awkward fan photos, and there are awkward fan photos that belong in the Hall of Fame. This picture definitely falls in the latter category. This photo features a fan who seems to be very good-natured, but also blissfully unaware that you’re supposed to stand closer to Katy Perry than where he’s currently standing. Jesus is not supposed to be able to get between you and Katy Perry, sir. And Katy, what’s up with the box braids? What’s with this outfit? What’s with this backdrop? Again, we have so many questions…

12. She Looks Thrilled

Katy Perry Awkward Fan Photos with Fans

Not every meeting with fans is going to go well, and there’s no better example of this than this picture — which is clearly one of a classic series of awkward fan photos with Katy Perry. In 2013, a paparazzo snapped a picture of Perry in New York City, where she looked to be wearing a blue kimono (a nice blue kimono, we think), and a crown of flowers that clearly looked like the prototype of countless terrible Snapchat filters to come. We’re not sure who looks more uncomfortable — the fan, who isn’t sure who Katy Perry is, or Katy Perry, who’s probably wondering how the hell things got to this point.

11. Will You Marry Me?

Katy Perry Marriage Proposal Awkward Fan Photos

There’s nothing that feels more like a kick in the cojones than when you’re asking the girl you love to marry you, and she turns you down. Apparently, however, someone forgot to tell this Katy Perry fan that, unless you’re actually dating Katy Perry (and he has about as much of a chance of dating Katy Perry as Donald Trump does), asking her to marry you on the Prizmatic World Tour isn’t romantic, it’s creepy. And that’s the origin of this picture, which is not only scary, it’s one of the most awkward fan photos we’ve ever seen. Katy doesn’t know where to hide first, and our collective hearts ache for her as she tries to deal with this clearly unbalanced fan.

10. The Leaders Of Generation Ex

Katy Perry and Jennifer Aniston Awkward Fan Photos

There are few things more uncomfortable than going out somewhere and meeting the ex-girlfriend of your ex-boyfriend. This meeting can go one of two ways — you can either hate each other on sight, and spend the night separated to prevent criminal charges, or you’re going to love each other and bond over the mutual experience of the ain’t-sh*t rat bastard. Or, you’re going to do what Katy Perry and Jennifer Aniston did here, and create one of the most awkward photos ever. The ladies — who both used to date John Mayer (fantastic taste there, ladies) — met at a party put on by Jennifer Meyer (Tobey Maguire‘s ex-wife — isn’t Hollywood incestuous?), according to E! News. Meyer is a mutual friend of both Aniston’s and Perry’s, but judging by this photo, we don’t think these two will be catching a cup of coffee together anytime soon.

9. Rollin’ With The Frenemies

Katy Perry Ruby Rose Awkward Fan Photos

Now that Katy Perry has been in the spotlight for a while, it’s only natural that she’d hang out with a few celebrities from time to time. Here, she’s pictured with Ruby Rose (remember when she was a thing? Yeah, that was fun…), and needless to say, Perry’s face turns this meeting of the celebrity minds into one of her many awkward photos. But it turns out Perry was right to feel uncomfortable around Ruby Rose: shortly after this photo was taken, Ruby Rose waded into the torrential waters that was the Katy Perry-Taylor Swift beef, taking Taylor’s side and dragging Katy’s new music for filth. Shortly thereafter, she deleted the nasty Tweets to Katy, saying that “being mean doesn’t suit me” and removed herself from the middle of the fracas. Too little, too late, we think.

8. When Granny Throws Shade

Katy Perry Grandma Awkward Fan Photos

As we mentioned earlier, Katy Perry grew up in an ultra-religious household, where not even eggs & mayonnaise were allowed unless they were called “angelled eggs.” So, it makes sense that her grandmother would be part of these strict religious beliefs, thus not knowing who The Smurfs were (to be fair, she probably thought they were shepherds of the devil; after all, they wear no shirts, and in the original comic strip by Peyo, they were quite subversive). Therefore, we have her to thank for this — one of Katy Perry’s most hilariously awkward fan photos — which was taken at the Smurfs Hollywood premiere. (Katy Perry, for those who don’t know, voiced Smurfette, the somehow sole female Smurf in the village…)

7. The Tattoo She Pretended To Like

Katy Perry Tattoo Awkward Fan Photos

There are few things more difficult to do than having to pretend to like something you think is utterly ridiculous. However, if you’re a celebrity of any kind — especially a mega-celebrity like Katy Perry — you have to fake it to avoid pissing off your fans. But while you can pretend to be nice for a little while, there will be certain “tells” on your face that will be evident to anyone with a pair of eyes. No place is this more evident than in this picture, which will go down in history as one of Katy Perry’s hilariously awkward fan photos. It seems as though this rather, uh, dedicated fan got a tattoo of Perry on her back…except it looks like it was drawn with a blunt Crayola crayon. Katy probably was like, “Oh wow, that’s so cool!” when she met the fan, but her eyes are clearly screaming, “Oh dear God, help me!”

6. …And Then Came This

Katy Perry Awkward Fan Photos Jingle Ball

The Z100 Jingle Ball in New York City is an annual event that, literally, shakes the rafters of the city that never sleeps. Featuring all of the hottest musical stars of that year, this event has become an annual Christmas tradition and, like the Rockettes, an integral part of a New Yorkers life. And it’s the 2010 version of Jingle Ball that features this picture, which is certainly one of the most awkward photos that Katy Perry has ever taken. She’s on her way to perform…but is she aware that she’s not a Rockette? That this is Madison Square Garden and not Radio City Music Hall? That the mustache isn’t necessary?

5. That Time She Thought This Dice Dress Was A Good Idea

Katy Perry Matt Lauer Awkward Fan Photos

Believe it or not, there was a time that Katy Perry still had to do breakfast television to get people to listen to her music. Such was the case in 2009, when she went on The Today Show (hosted by Matt Lauer) to sing “Hot and Cold” live for the first time. When asked about this dress — which she claimed to make herself — Katy said that she was a “sucker for themes” and wanted to make this performance all about Vegas. But this picture — one of Katy Perry’s many hilariously awkward photos — was taken right after she had a bit of a performance malfunction. She tried to get the guitar she wanted to play over the dress, and it wouldn’t fit. Embarrassing! “Now I feel really stupid. This is a stupid outfit. You can have it afterward,” she said to Lauer.

4. This Is How She Announced Her Collaboration, Maybe, With Ariana Grande

Katy Perry Awkward Fan Photos With Ariana Grande

We’re not going to get in Katy and Ariana’s collective butts too much with this picture, since they’re friends in real life (so they’re going to joke around from time to time), they’re due to be collaborating on a song, and Katy was the first to step up when Ariana Grande announced that she would be hosting a benefit concert for the victims of the Manchester attacks at her concert. Still, what makes this photo one of Katy Perry’s many awkward photos is the fact that she doesn’t look too pleased to be doing what Ariana seems to love to do on a daily basis (which is…that, we guess). I mean, what is this supposed to indicate? A cat? A tiger? A bear? What, you guys?

3. A Girls’ Night Out That Was Posted And Deleted

Katy Perry Ellie Goulding Lorde Kelly Rowland Awkward Fan Photos

When you go out with your girls, there’s always some type of drama, and you know that you’re prettier than the rest of them, and so on and so forth. But when Katy Perry goes out with her girls, she brings Lorde, Kelly Rowland, and Ellie Goulding out to party their pants off. And, as you can see from this photo above, they were having a blast. But what makes this photo one of Katy Perry’s many awkward photos is the fact that this was posted on Ellie Goulding’s Instagram, where it got over 600,000 likes…and then she deleted it. This caused quite a stir in Katy Perry’s fandom — because they were wondering what, exactly, had crawled up Ellie Goulding’s butt — but Ellie explained that it was simply because she “couldn’t remember” what all went on that night. Must have been a hell of a night…

2. Girls’ Night Out, Part Deux

Katy Perry Awkward Fan Photos

In 2013, Katy Perry attended the Nickelodeon Kids Choice Awards, and somehow, Kristen Stewart and Selena Gomez both managed to find a way to sit on her lap. This, alone, makes this one of the most awkward photos that all of these ladies have ever had to take. But let’s take a look at some of the more ridiculous elements of the photo outside of everyone’s uncomfortable facial expressions. First, the dresses. What the hell is everyone wearing? Second, there’s the shoes that Katy is holding. Yes, they’re Louboutins — excellent taste — but who do they belong to? Why isn’t someone wearing their shoes? We have so many questions and not enough answers.

1. Welcome To Goodburger, Home Of The Goodburger, Can I Take Your Order Please?

Katy Perry Keenan Thompson Awkward Fan Photos

What. Is. Happening. Here? First of all, for those who don’t know Keenan Thompson, he got his start on Nickelodeon’s hit kids variety show All That, and he — along with his co-star Kel Mitchell — created the Keenan and Kel show, and the Goodburger skit (which eventually became a movie of the same name — the punchline of the skit is the title of this slide. Not funny? Guess you had to be there…). Most recently, he’s been featured on Saturday Night Live, where he played President Barack Obama. In other words, he’s a really funny guy. But in this — one of Katy Perry’s most awkward photos — he looks anything but amused at what the “Hot and Cold” singer is saying. And, not for anything, that dress is positively awful. It looks like an Etsy shop threw up all over her.

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