Welcome to the time machine of teenage turmoil—our very own walk of shame down memory lane! This week, I’ve dived headfirst into the cringe-tastic world of r/BlunderYears to bring you a collection of awkward photos that are so painfully hilarious, they could only come from the depths of our youth. From hairstyles that defied gravity (and good taste) to fashion choices that scream “what was I thinking?!”, these nostalgic pictures remind us that puberty wasn’t just a phase—it was a full-blown style disaster.
So, pull out your old yearbooks, brace yourself for some serious flashback frights, and let’s revel in the glorious awkwardness of our past selves. Trust me, it’s therapy you didn’t know you needed!
1. 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?!
Blunder Years
2. At 15 we ran a lesser known but well respected offshoot of the Crips in Berkshire, England.
Blunder Years
3. Dear diary, mood: apathetic
Blunder Years
4. Don’t ask me why the Kindergarten’s photographer decided to portray 5 year old me as a communist leader
Blunder Years
5. For some reason my younger self decided to try and shave my eyebrows. The day before 1st Grade school pictures.
Blunder Years
6. How I went to senior prom in 2000
Blunder Years
7. I made the Jersey shore look like proper dandy’s. (Douche cringe) 20+ years ago
Blunder Years
8. I was trying to smile like a Ninja Turtle. Doesn’t translate well when actual humans attempt it.
Blunder Years
9. I wore this vest and fedora combo everyday on that trip. The concierge at our Disney resort said “I dont trust this guy” about me and my fedora.
Blunder Years
10. In 7th grade I photoshopped myself marrying Andy Biersack…
Blunder Years
11. Kindergarten, late 80s
Blunder Years
12. Me thinking I was cool with my pet crow in 2003
Blunder Years
13. My first ever school picture. I’m told it made my mother cry.
Blunder Years
14. My First Facebook Profile Picture, Circa 2008
Blunder Years
15. My mother used to call me megamind. Circa 2013
Blunder Years
16. My wife’s favorite picture of me
Blunder Years
17. Our band picture, we never actually learned to play instruments, Circa 2009
Blunder Years
18. Refused to wear anything but the sweater on picture day. Mom and I eventually found a compromise by adding the collar polo.
Blunder Years
19. Studying the blade runs deep in my blood.
Blunder Years
20. 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.
Blunder Years
21. Yes, I really wore this to school…
Blunder Years
22. yes that is my real head, no this photo was not edited.
Blunder Years
23. When I ran for 5th grade class president
Blunder Years
24. 15 years ago. (If you care about the integrity of hair you don’t want to know how I achieved the tie dye looking bangs, and no…. My eyebrows never grew back 3x thicker than before shaving them despite my wishes.)
Blunder Years
25.
Blunder Years
26. I was 12 and I wore this t-shirt proudly to school.
Blunder Years
27. My boyfriend used to cut my hair with a Flowbee, and I got stoned and let my friend shave my eyebrows off and had to draw them back on for months
Blunder Years
28. Senior Portraits Part 2: Electric Boogaloo
Blunder Years
29. My wife framed this atrocity. 7yrs old in 1987.
Blunder Years
30. Prom 2004
Blunder Years
31. Putting cigarettes out on my shoulder to look “cool” Circa 2013
Blunder Years
32. Senior Portraits Part 2: Electric Boogaloo
Blunder Years
33. The 80s were rough.
Blunder Years
34. The year was 2012 and my buddy and I dropped the heaviest country inspired anti system EP of the year
Blunder Years
35. Went to school as a girl for Halloween, Circa 2007
Mike Primavera is a Chicago-based comedy writer even though he doesn't HAVE to work. He lives comfortably off of his family's pasta fortune. Follow him on all social media at @primawesome
Mike
