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15 Cringeworthy Ways Older People Try to Stay Hip and Relevant

Elderly may exhibit signs they're connecting with Gen Z. "What indicates an older person trying to seem cool?" asked an online user. Top responses:

THE CLASSIC SKATEBOARD LOOK

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

MADONNA’S PUBLICITY STUNTS

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

PINK TRACKSUIT AND NO HOUSE RULES

“Pink tracksuit and no rules in their house,” said one.  “I’m not a regular mom; I’m a cool mom,” another added. 

COMPLEMENTARY T-SHIRTS

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

SKINNY JEANS AND EAR-PIERCING

"Saw a guy in his late 40s having an affair. Started wearing skinny jeans, pierced his ear, and sported a crazy haircut. Complete bozo!"

CONFORMING TO ALL FASHION TRENDS

"Embrace aging by finding your unique style, not by following every fashion trend. I won't give up my skinny jeans, but my nap dress got me through hot August days!"

USING DEAD MEMES

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

PURPLE HAIR

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

HIP-HUGGING PANTS

“Jeff Bezos in his hip-hugging pants.” 

USING TEENAGER SLANG

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

BUYING ALCOHOL OR DRUGS FOR TEENAGERS

“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.” 

A BLACK CONVERSE

“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.”

NIGHTCLUBS

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

DRAKE

“Everything about Drake.”

A RIDICULOUS SPORTS CAR

“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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