A tweet from DeShon Elliott stating, “NFL partnered with Microsoft but they can’t get us the new Xbox for free is very sickening.”
via Canva

There’s that distinct flavor of discomfort that stems from bearing witness to a stirringly awkward moment. It’s not your own, but like someone else’s, and you can pick up on the secondhand cringe feel in the process. These awkward photos are particularly adept at generating a deep sense of cringe.

1. It’s so obviously not a face swap

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shitemike40/via reddit.com

2. He sent a group message instead of separate messages to each woman

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3. It was just a camo joke…

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4. “Is that clear?”

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5. Rihanna is trying to swim in peace

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6. Why would you willingly etch that into your body?

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7. A multi-millionaire is sick that he can’t get a new Xbox for free

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8. This is what happens when you try to microwave your cash to get rid of bacteria

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9. This is worse than leaving no tip

kremlinhoosegaffer/via reddit.com

10. Ask and you shall receive

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11. They misunderstood the assignment

daslkopwrt/via reddit.com

12. No, magicians enter the rabbit realm

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13. Don’t test him

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14. He’s at Disney

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15. “That awkward moment”

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Explore more cringeworthy internet moments:

Check out 20 People Who Refused to be Honest Online, or take a look at 25 People Who Have No Sense of Humor (And The Internet Noticed). Finally, if you want to see people with no common sense, check out 21 People Who Clearly Lost a Battle With Common Sense (And the Internet Noticed).

Meet the Writer

Matt has spent over the last 8 years as both a writer and editor, working in Seattle and Brooklyn, where he is now based. He loves escaping the tirelessly fast pace of the “Mad Apple” that is NYC by taking walks and runs through parks where he’s able to catch up on the latest tea about society from the city’s ever chatty, always hungry, occasionally maniacal, pigeons. They always have a lot to say. When he’s not taking his urban nature strolls, or dutifully combing the deepest rabbit holes of the internet to find the content that’s worth sinking your mind’s teeth into, he’s likely holed up at a dark-lit dive bar with a new book and/or some friends, or just as easily he could be on the hunt for the next addition to his steadily growing plant family.

These days Matt’s caught up in trying to provide folks as many vivid glimpses into the days long since passed as he can, through fun and engaging collections of hand-picked vintage photos.