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15 Cringeworthy Ways Older People Try to Stay Hip and Relevant

As people grow old, they exhibit certain signs that indicate that they are trying their best to come off as cool and become one with Generation Z. An internet user asked, “What is something that screams ‘this older person is trying to seem cool and young’?”. Below are the top responses:


2. skateboard

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“Wearing a red jacket over a gray shirt and a red cap, carrying a skateboard, and asking his fellow kids how they’re doing.” 


Excited girl dressed in red casual and glasses opened mouth in surprise and bulged eyes against yellow background, isolated. Portrait of shocked woman with glasses

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“Almost everything Madonna has done in the last ten years to remain relevant desperately.”


Young beautiful redhead woman wearing casual sweater over isolated pink background clueless and confused with open arms, no idea concept.

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“Pink tracksuit and no rules in their house,” said one. 

“I’m not a regular mom; I’m a cool mom,” another added. 


cheerful woman orange sweatshirts sunglasses multicolored glasses supply yellow background unaltered. High quality photo

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“I recently suggested that my husband and I get T-shirts with ‘Based Mom’ and ‘Chad Dad.’ My kids were not impressed.”


stupor surprised funny face expression

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“I saw a guy having an affair, and he was in his late 40’s to early 50’s. He started wearing skinny jeans, got his ear pierced and shaved the sides of his head with hair longer on top so it swished around. Complete bozo!” 


Romantic mood. Girl in love dating. Obsession concept. Fall in love. Girl adorable fashion model makeup face hold heart valentines card. Love from first sight. Woman in stylish dress hold symbol love.

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“Being a victim to all the fashion trends. I used to work with someone like that. Part of the fun of getting older is finding your style and not having to worry so much about what’s cool and what’s not and picking and choosing what new items you like.

For example, I’m not giving up skinny jeans/jeggings anytime soon, but my nap dress got me through the sticky days of August!”


9. crazy woman 1

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“Teachers putting memes from 2010 and dead trends from the late 2010s into their slideshow.”


crazy woman with pink hair

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“I’m a kindergarten teacher with purple hair. Five-year-olds think I’m cool.” 


middle age woman feeling stressed and anxious, depressed and frustrated with a headache, raising both hands to head. night suit concept

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“Jeff Bezos in his hip-hugging pants.” 


Close up photo portrait of funny funky playing fool making faces she her girl sticking tongue out watching in different ways isolated pastel background.

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“Using teenager slang. They always make it sound so weird and awkward.” 


Disheveled drunk or female high on drugs at a nightclub

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“Adults buying alcohol or drugs for teenagers. They weren’t popular when they were kids, so they do this to seem cool and young to teenagers.” 


Portrait of funny wondered adult blond woman looking at camera with idiotic silly comical expression, making fish face with lips, stupid duck grimace. indoor studio shot isolated on green background

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“I got my first black Converse at 55. It might seem like I’m trying to be cool and young. I’m trying to be Debbie Harry, cool and old.”


Cocktail glass with drink in the bar with bottles in the dark background

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“Nightclubs, not all, but some are cringe to hang out past a certain age.”



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“Everything about Drake.”


Portrait of Young girl driving cabriolet at sunset.

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“A ridiculous sports car. I have a race car in my garage, a Cherry Shelby GT500 that I rarely drive. I’m about to be 69 years old, and I drive carefully anyway. I drive my Jeep.”

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Portrait disappointed lovely girlish feminine youth impressed astonished horrible terrible gossip rumor secret irritated scandal unbelievable unexpected modern summer clothes isolated green background.

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Photo of crazy funny young nerdy man stick tongue out fooling face joke isolated on blue color background.

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Young caucasian woman isolated on blue background forgetting something, slapping forehead with palm and closing eyes.

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This article was originally published on Mrs. Daaku Studio.