Top Definition
To engage in a wild spree.

Origin: The alussion is to the kind of riotous behavior that results in red blood being spilt.
K: I'm pissed. Wanna go paint the town red tonight?
J: Let's do it.
by Kaileyxx July 09, 2005

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to go on a wild drinking bout
What ever you do, don't paint the town red on a holiday.
by Light Joker December 05, 2006

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To go to various different parties in different parts of town, or basically party all night long.

The expression "paint the town red" has NOTHING to do with a girl on her period leaving spots of blood all over the town. (Where do people get this shit?)
Guy 1: "I'm bored as hell. I heard Jake invited a bunch of hot chicks to his party tonight?"
Guy 2: "Yeah. Let's go paint the town red, man."
by PaintTheTownRed? July 13, 2010

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To go out and have a good a time. Usually, but not requiring, the aid of alcohol or other mind altering substances. The phrase come from an Englishman who after a fox hunt (because that's what the British do ) got so drunk with buddies that they literally found some paint and proceed to go all extreme makeover: village edition on the town.
You frank, wanna go paint the town red later?
by Not that guy you think I am. September 02, 2010

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To have violent intercourse with a woman while she is menstruating.
Dude 1: I'm about to have some super-hardcore sex with my girlfriend.

Dude 2: Isn't she on her period?

Dude 1: Yeah. I'm about to Paint The Town Red

Dude 2: That's gross.
by Jon Jacob Jingleheimer Schmidt October 08, 2010

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when a girl is on her period and she wanders the street with a skirt/dress and no underwear on dotting the streets with blood.
Nicole: Steve donkey punched me last night, I think I am going to blow off some steam and paint the town red. Lisa, can I borrow your white skirt?
by sharting sesame seed February 26, 2009

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Accidental menstruation on public property including buses, restaurants etc. for an extended amount of time.
I like, way spaced on tampons and had to paint the town red today.
by Heat* April 23, 2007

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