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.
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.
to go on a wild drinking bout
What ever you do, don't paint the town red on a holiday.
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."
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?
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?
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.