"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 03, 2011
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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 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 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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When members of Team Valor go from gym to gym in Pokémon Go, battling them and claiming them for Team Valor, it is said that they are painting the town red.

For Team Mystic is is called painting to town blue.

Towns do not get painted yellow very often due to the lack of number of players on Team Instinct.
Her and I went out last night to play Pokémon Go, we were painting the town red.
by Arceus777 September 20, 2017
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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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