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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

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.

Mile Road 

Make up most of the major east-west roads of Detroit's northern suburbs. The miles are measured going north from the intersection of Woodward & Michigan in Detroit. They include the infamous 8 Mile Road, the dividing line between Detroit's generally wealthy suburbs and more impoverished inner city. The mile roads are numbered up to 37.
"Where's Oakland Mall?"
"At 14 Mile Road & John R."
Mile Road by cds19 December 22, 2008

mile high road head 

when a vehicle operator receives oral sex while in control of an aircraft.
I heard a rumor that mile high road head was the only way Lindbergh survived that Atlantic crossing.
mile high road head by topgunmav October 20, 2010

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