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100 miles of bad road 

When a man or woman's face is extremely ugly!!!
person1)Man, she looks good!
person2)Her face looks like 100 miles of bad road!
100 miles of bad road by horsefly October 10, 2005

like a mile of bad road 

Not as ugly as 100 miles of bad road but still not as good looking as you would liked it to be.
You guys make great babies.Ours look like a mile of bad road.”

Quote from Black Mirror episode Striking Vipers
like a mile of bad road by IKISME December 20, 2020

looking like five miles of bad road 

Southern expression meaning someone or something looks severely disheveled, exhausted or sloppy, like an old road in desperate need of repaving.
She woke up the morning after the party looking like five miles of bad road

Fifteen Miles of Bad Road

When someone, as they age, goes from looking hot to looking like fifteen miles of bad road
Have you seen Lia? She was hot in high school! She looks like fifteen miles of bad road now.

The Bad Girls At The End Of The Road

A group of evil females who live at the end of the road.

To engage in naughty behavior on innocent people who haven't been corrupted by smutty fanfiction.
"Then these bad girls showed up and took me to their evil lair"

To the bad girls at the end of the road, being bad never felt so good.