50 Funniest “Regrettable Past” Moments You Can’t Help But Relate To

Cringe at your teen years? Join the laughs with 'Blunder Years' and see we’ve all been there!

Damjan

• Published in Interesting
• October 22, 2024

Almost everyone has moments from their younger years that they wish they could forget. Back then, we thought we were cool, whether by following the latest fashion trends, trying out bold hairstyles, or using the slang of the time.

Growing up, we were convinced we knew what was “in,” but looking back now, those old photos often make us cringe. "Blunder Years" describes that awkward phase in our youth when we thought we were nailing it but later realized our choices were embarrassing.

Most of us have photos from that time that make us laugh and cringe, from weird outfits to strange hairstyles. But these awkward moments also remind us how much we've grown and changed since then.

Many of us were just copying what we saw on TV or trying to follow the fashion of the time, whether that was leg warmers, neon colors, or heavy makeup. For those who want to laugh at their past and feel a little better about their teenage mistakes, there’s a popular online community on Reddit called "r/blunderyears."

With over a million members, people share their most awkward and embarrassing photos from their younger years. It’s a place where everyone can laugh together and realize that no one went through their awkward phase alone.

What makes the subreddit so fun is that it turns those embarrassing memories into something lighthearted and cheerful. People post photos of their worst hairstyles, strange outfits, and cringe-worthy moments, all for the sake of a good laugh.

It’s a place where everyone can share their awkwardness and find comfort in knowing that we all made silly choices when we were younger. Here are some favorites to enjoy (and maybe even relate to).

"High School Senior Photo 2007"

"8th Grade, Dared To Wear Thongs And Sock Stuffed Bras To School. We Did"

"Mom Asked Me To Model For A “Moody” Photo Shoot. Peak 7th Grade Me"

"Homecoming, Senior Year 2003. Attending The Old Football Dance To Complain About The Music And Sulk About"

"Mil Killing It With Another Share: Husband Age 14"

"9 Year Old Cousin: Stepped Out Of Vogue. 8 Year Old Me: Stepped Out Of An Episode Of South Park"

"Me, Circa ‘05, 6 Years Before Bob’s Burgers Came Out"

"My College Rebel Phase Was To Be The Opposite Of My Hippy Dippy Parents"

"I Think This Hairstyle Was A Thing?"

"I Didn't Even Play Guitar"

"Thought I Was Cool With My "Spike Hair" No Wonder People Used To Say It Looked Like A Tsunami"

"Dear Diary, Mood: Apathetic"

"My Mom Is Coming Out Of Her Bridesmaid's Dress, My Dad's Eyes Are Closed, My Brother Has His Finger Up His Nose, My Sister Has A Hand In Her Mouth, And I Am Over Being A Flower Girl"

"My Freshman Yearbook Photo (2014)"

"Bring A Prop For School Pictures. Most Kids Brought Sports Equipment Or An Instrument. I Brought... my Ventriloquist Dummy"

"I Looked Ready To Join The Golden Girls By The Time I Was 7 In 2004. Can You Tell I Wasn’t Pleased?"

"I Can Guarantee Protection"

"Almost 25 Years Ago... I Used To Wrap My Hair Up With Things. This Is My Last Year Of High School Year Book Photo. 17 Years Old. Phone Cord Head Band. So Stylish! What's A Phone Cord?!"

"My Wife Framed This Atrocity. 7yrs Old In 1987"

"My Friends & I Rocking Our Zoot Suits During The Swing Craze In The 90s"

"That Time I Wanted To Be A Denim Druid"

"My Fiancé Saw This Picture My Parents Took Of Me On A Cruise Ship And Laughed Until She Cried"

"I Hear This Is The Sub For Those Who Have Studied The Blade"

"Went To School As A Girl For Halloween, Circa 2007"

"1995-1997 My Dear Grandpa Showed These To My Fiance The Night Before Our Holy Matrimony"

"I Got The Jacket From The Lost And Found Box And Spray Painted My Shoes Gold In Welding Class, Myspace Delivered Too Hard Circa 2007"

"My Friends And Family Let Me Leave The House Like This. It Was 1984, And I'm 15"

"My 1994 High School Senior Yearbook Picture"

"I Was Trying To Smile Like A Ninja Turtle. Doesn't Translate Well When Actual Humans Attempt It"

"When I Was 13 My Mom And I Had Some Fun After My Deadbeat Dad "Gifted" Me A Trash Bag Of His Girlfriend's Clothes, Left On Our Front Porch"

"Grandma Took Me To Get Glamour Shots At The Mall- Mom Said She Almost Had A Heart Attack First Time She Saw The Photos"

"Yes, I Really Wore This To School…"

"Used To Wear This Bunny Suit Long After It Was Age Appropriate And Theme Appropriate... In This Photo, It Wasn't Even Easter, It Was Someone's Birthday"

"The Fear Is Real. Age 15, Caught Dancing By Myself In My Room"

"My mother roasted me by sending this pic in a massive group text. "

"15 Years Ago"

"The Chill That Crawled Up My Spine When This Came Up On My Timeline"

"Oh My God"

"My 8th Birthday. I Was The Only Kid That Knew How To Party"

"Old Lady In The 80’s"

"I (Female) Insisted On Dressing Up As Steve Wozniak For 'Historical Figures' Day In Elementary School"

"Was Feeling Myself After Finding A Loose Tassel From My Friends Couch Pillows"

"My First Ever School Picture. I'm Told It Made My Mother Cry"

"It Was So Scratchy"

"Me - 5 Years Old, Around 1991/92"

"By The Third Grade I Was Dressed For My Midlife Crisis"

"4th Grade 1991, Laser Background, Big Wire Frame Glasses And Ministry Shirt. Doesn't Get Much More Early 90s Than This"

"Me Rockin' TF Out Of A Mullet And Living My Best Life In Hawaii 1994"

"Looking Back At This Mother-Daughter Photo Shoot At Disney, I Can See My Mom Was Trying So Hard To Bond With Me… Her Angsty, Awkward 13yo Daughter"

"My Husband, Circa 1987"

"How I Went To Senior Prom In 2000"

Everyone goes through their "Blunder Years," and it’s nothing to be ashamed of. These embarrassing moments are part of growing up and figuring things out.

Whether it was weird fashion choices, questionable makeup, or strange hairstyles, we’ve all been there. Laughing at these memories, especially with others who have been through the same thing, is a great way to embrace the past and appreciate how far we've come.

Damjan