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Funny yearbook photos capturing awkward teenage years of a girl with dark eye makeup, red lipstick, and pigtails.
Funny,FailsNOV 7, 2026

67 Yearbook Photos That Are The Perfect Example Of One’s Awkward Teenage Years

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One’s teen years are always awkward, which is ironic given that it’s probably the time one is most self conscious about how they are perceived. It’s also a time where people try new looks and really experiment with their identity.
So we’ve gathered some of the most hilariously awkward and random yearbook pics from across the internet. Get comfortable as you scroll through, brace yourself for some second hand embarrassment, upvote your favorites and if you’ve ever had some questionable photo choices in high school, share your story in the comments below.

#21

Awkward teenage years yearbook photo of a smiling guy posing with an electronic keyboard.
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10points

Real smiles tend to reach the eyes only when people feel relaxed, so what the camera usually catches is a polite grimace. Add hair styled by a parent in the car, a shirt chosen under pressure, and the fact that many students are in the middle of an awkward growth spurt, and you have the recipe for a legend.

#22

Alternative goth style teen girl wearing mesh top and round glasses posing for unique yearbook photos.
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9points

#23

An awkward teenage years yearbook photo featuring a young man with a spiky mullet hairstyle and tuxedo.
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9points

#24

Student quote about skipping class featured in humorous yearbook photos.
9points

And then there is the pressure. A yearbook photo is not a snapshot that vanishes into a camera roll. It gets printed in a book, handed to hundreds of classmates, and stored in a closet for decades, which means every flyaway hair earns its own permanent record. Even the famous are not safe. Conan O’Brien has apparently ordered five extra copies of his Harvard yearbook over the years because his own copies kept getting destroyed, as reported by The Harvard Crimson.

#25

Funny portrait in a collection of awkward teenage years yearbook photos showing heavy makeup and high pigtails.
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8points

#26

Young man posing with his cat against a laser background in awkward teenage years yearbook photos.
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8points

#27

Awkward teenage years yearbook photos showing two girls posing with chocolate muffins.
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8points

Then there are the backdrops. In the 1980s plenty of school portraits featured glowing, criss crossed laser lines, a look that was considered fashionable at the time. Years later a Tumblr called We Have Lasers gathered the evidence, and Time treated the laser backdrop as the ultimate shorthand for an awkward childhood photo, right up there with braces and enormous bangs. A mottled blue backdrop, a stiff pose, and a tilted head joined the party.

#28

Funny yearbook photos showing multiple students with the surname Lee in a row.
8points

#29

Side-by-side yearbook photos showing two teenage boys with matching suits and funny quotes.
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8points

#30

A vintage yearbook photo portrait of a young boy smiling at the camera.
8points

The good news is that the evidence will last. Lifetouch, a major school photo company, says its portraits are printed on paper meant to resist fading for up to a hundred years. So the pictures in this list are not going anywhere. Be kind to the faces below, because every one of us has a laser backdrop somewhere in our past.

#31

Awkward teenage years yearbook photo of a girl holding a winking cat with a large cat background.
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7points

#32

Black and white yearbook photo of a young woman named Floy Harbin with volumized hair showing awkward teenage years styles.
7points

#33

Retro school portrait of a young woman with perm hair and bangs highlighting awkward teenage years style trends.
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6points

#34

Vintage portrait of a smiling teenage boy with glasses and a mustache featured in retro yearbook photos.
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6points

#35

Teenage boy holding a large Pikachu plushie in one of many awkward teenage years yearbook photos.
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6points

#36

Awkward teenage years yearbook photo of a teenage boy making a funny, startled facial expression.
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6points

#37

Awkward teenage years yearbook photo of a smiling girl with big glasses, braces, and a mullet hairstyle.
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6points

#38

Awkward teenage years yearbook photo of a young man wearing glasses and a pink tie, proudly holding a computer keyboard.
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6points

#39

Awkward teenage years yearbook photo of a boy in a traditional Scottish kilt with a trophy.
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6points

#40

Young man posing in a Batman-themed outfit for an awkward teenage years yearbook photo.
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6points
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