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 9, 2005
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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 3, 2010
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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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killing people while their blood is splattering around the town, making it red.
“you little fuck head, you should be dead, i’ll pull up in a coffin and paint the town red.” -zillakami
by Fat Mama Joe June 11, 2022
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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 27, 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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"Painting the town red" means to party, run wild, and have fun. It can also be used to express the need/want to surprise and gain the attraction of the opposite gender (as seen in example 2).
Example 1:

On the phone one lonely Friday night...

Ring Ring!

Sally: Hello?

Joe: Hey, Sal. It's Joe!
Sally: Oh, hey Joe... How are you tonight?
Joe: I'm good. You?
Sally: I'm alright... I just finished my homework, and... I'm alone. Karmen was going out to eat with Jeremy, and Lillyanna was going to a party with Annie, so I'm just going to eat and go to bed after some Facebook.
Joe: Oh, I'm sorry...
Sally: Well, if you'll excuse me, I've got to go-
Joe: Wait! How would you like to go out with Tony and me tonight? We're going to party and do some painting the town red after a few drinks at the Irish Pub downtown!
Sally: Really? Joe, that sounds awesome! Here, can you pick me up in an hour?
Joe: Sure thing, Sal!
Sally: Bye!
Joe: Adios.

Example 2:

Joe and Tony arrive at Sally's house an hour after the phone call...

Joe: Sally? You in here?
Sally: Yep! How do you like my outfit?
Tony: Whistles Sally, you look... sexy!
Joe: Sally, you...
Sally: Cleavage, huh?
Joe and Tony: Yes MA'AM!
Sally: Well, what are we waiting for? To the pub!
by InsanityisSexy:) October 3, 2011
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