23 Awkward Phase Photos That Are beyond Cringeworthy

Nathan Johnson Published 08/20/2021 in Funny

Listen, I once had long red hair that I may or may not have straightened to look like some iteration of Carrot Top playing in an emo band. We've all been there.

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1.
I let some trippy goths do my makeup, circa 2011.
2.
When I was around 4 or 5, my favorite toy was a coyote pelt named Emily. My parents and friends hated it so much.
3.
14 years old, at the height of my 'Hunger Games' obsession. The bow isn’t even mine.
4.
I couldn’t even take a normal picture with my grandma…
5.
The most ’80s room there ever was (sister and me, 1989.)
6.
I thought I was so cool and sophisticated (featuring the family portrait in my mom’s bedroom.)
7.
16-year old me fronting my first band.
8.
Me showing off my vampire books in my Mr. Bean shirt.
9.
Wife’s family glamour shot in the '80s with younger brother added in “seamlessly."
10.
When you’re trying to be edgy but Mom wants a picture.
11.
This is me around 12 years ago. The emo phase hit me hard.
12.
10 years ago. Growing up in a small logging town, it’s a wonder I wasn’t picked on more than I was in high school.
13.
Old school cool.
14.
My aunt asked me if I wanted to go shopping and get my hair done one day in 1985. This was the result.
15.
1997, Epcot. My parents love to bring this picture out and tell folks to meet “Helga."
16.
I wish I still had this cardigan.
17.
Thought this would fit here…
18.
My awesome high school senior photo, 2003.
19.
4 going on 40 with this ’90s glamour shot.
20.
13 summers ago, I had my sisters flatiron my hair all the time so I could look "like a Final Fantasy character.” Pics still taken by mom though.
21.
This was me at 16…I’m a dude.
22.
Somehow, this is my actual second grade public school photo.
23.
I love/hate how I chose every part of this photo including the dark brown eyeshadow.

1.
I let some trippy goths do my makeup, circa 2011.
2.
When I was around 4 or 5, my favorite toy was a coyote pelt named Emily. My parents and friends hated it so much.
3.
14 years old, at the height of my 'Hunger Games' obsession. The bow isn’t even mine.
4.
I couldn’t even take a normal picture with my grandma…
5.
The most ’80s room there ever was (sister and me, 1989.)
6.
I thought I was so cool and sophisticated (featuring the family portrait in my mom’s bedroom.)
7.
16-year old me fronting my first band.
8.
Me showing off my vampire books in my Mr. Bean shirt.
9.
Wife’s family glamour shot in the '80s with younger brother added in “seamlessly."
10.
When you’re trying to be edgy but Mom wants a picture.
11.
This is me around 12 years ago. The emo phase hit me hard.
12.
10 years ago. Growing up in a small logging town, it’s a wonder I wasn’t picked on more than I was in high school.
13.
Old school cool.
14.
My aunt asked me if I wanted to go shopping and get my hair done one day in 1985. This was the result.
15.
1997, Epcot. My parents love to bring this picture out and tell folks to meet “Helga."
16.
I wish I still had this cardigan.
17.
Thought this would fit here…
18.
My awesome high school senior photo, 2003.
19.
4 going on 40 with this ’90s glamour shot.
20.
13 summers ago, I had my sisters flatiron my hair all the time so I could look "like a Final Fantasy character.” Pics still taken by mom though.
21.
This was me at 16…I’m a dude.
22.
Somehow, this is my actual second grade public school photo.
23.
I love/hate how I chose every part of this photo including the dark brown eyeshadow.