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1.
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
550 221
 
2.
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
386 213
 
3.
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
199 118
 
4.
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
112 73
 
5.
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
26 211
 
6.
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
77 471
 
7.
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
64 460