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This Guy 2

Be careful what you wish for, ladies.

(submitted by Gray)

First Day

“It was the first day of school in 1989. Dan had an incident blowing up his bike tire and had to wear an eye patch, Andy is all kinds of nervous, and Joe is proudly saluting in wet pants.”

(submitted by Martha)

Bareback

It’s a beautiful day for an ostrich ride.

(submitted by Blake)

Now And Then

(via Awkward Years Project)

Scared Strait

(via CargoCollective)

Recreating the Awkwardness 3

(submitted by Kristen)

Hat-Trick

Clearly, she wasn’t happy with it either.

(submitted by Karna)

Spotty

“Just found this gem today. Apparently my mother thought it was appropriate to take me to a rave in a dalmation outfit. Needless to say, I was not happy.”

(submitted by Nicholas)

Lean On Me

He had a really good support system.

(submitted by Laura)

Uncle Wally

“Uncle Wally is not a very good babysitter.”

(submitted by Liz)