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26 Nostalgically Cringeworthy Photos Of Things We All Did As Kids

Two nostalgic images.

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Published July 04, 2025

Published July 04, 2025

Let's face it, everyone has done something in the past they are ashamed or embarrassed of. Whether it was a weird fashion choice made to go to school in, some odd hobby that seemed impressive at the time, or following a popular trend that is just ridiculous now. These cringeworthy moments haunt everyone from time to time, but even more so if there is picture evidence of those terrible moments.

School photos, family trips, and selfies from the past reveal the insane choices people made during their adolescence. These photos may be super embarrassing, but at the time everyone thought they were so cool. Looking back on them might make someone want to crawl into a hole, but the enjoyment others can get out of them might just make it all worth it.

Here is a collection of cringeworthy yet nostalgic images people have shared of the embarrassing things they did as children and teenagers. The emo phases, the gamers, the nerds, and the young fashionistas have all come together to share the weird kid in all of them.

1996, I sewed my own dog vest and loved it so much

(Source: Reddit)

Me after I discovered Photoshop in the early 2010s

(Source: Redd)

As a 10 year old…

(Source: Redd)

2004, trying to take a MySpace photo while no one was home

(Source: Redd)

I really thought I was a MySpace Queen

(Source: Redd)

Thought it would be cool the make KNEX body armor

(Source: Redd)

My favourite photo of my wife as as child, 2003

(Source: Redd)

On a road trip in 2004, obligatory angsty teens against a picturesque background

(Source: Redd)

14-year-old me during my Eminem phase, that's a hairbrush hanging from my lamp

(Source: Redd)

Learned my lesson about taking a razor to my eyebrows

(Source: Redd)

Hawaii wasn't ready for my ice cold sister and I in 2003

(Source: Redd)

Me at 13 in 2011, waited for 3 hours in the heat to meet Freddy from iCarly

(Source: Redd)

My childhood was destined to be a rough one

(Source: Redd)

Me, a girl, trying to impress my crush by being one of the guys, on the right

(Source: Redd)

1996 high school yearbook photo

(Source: Redd)

2002 school photo

(Source: Redd)

Got really into Photoshop in 2009

(Source: Redd)

Mother and son photo, 1992

(Source: Redd)

The photo that started it all…

(Source: Redd)

Me in 2016, I was Melanie Martinez's biggest fan

(Source: Redd)

It was the '70s…

(Source: Redd)

14-year-old me Photoshopping my dad for Britney Spears

(Source: Redd)

Homecoming, 2012

(Source: Redd)

This is a senior photo

(Source: Redd)

Senior prom photo from 2000

(Source: Redd)

Junior year, 2002, rural Midwest

(Source: Redd)

Tags: blunder years, cringe, nostalgia, throwbacks, throwback, history, nostalgic images, cringeworthy, cringe photos, nostalgic cringe, cringeworthy nostalgia, facepalm, facepalm moments, 90s, '90s, 1990s, '90s nostalgia, '80s nostalgia, 1980s nostalgia, 2000s,



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