"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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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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A online video-game where you play as the Minecraft character "Steve" except you get to brutally murder everyone you see. Players get the option to play in a story-mode type gameplay with a story about some fucking alien bullshit, but you still get to murder all the aliens. Other options include multiplayer gameplay, single-player gameplay, and an arena style gameplay with higher levels of difficulty with each arena you pass.

The game was initially released on October 13th, 2015 by South East Games and only meant as a console game for the Play Station 4. But, was later released to other consoles like Xbox and Nintendo Switch, it was later playable on PC after the game was added for sale on the Steam Game Store.

Now you may be wondering, why the fuck would I spend 20 dollars on a game where I just beat the living shit out of everyone? Well let me tell you my friends, if you are in a bad mood this game will make you happy almost instantly. You can let all that anger and sadness go into ruining people in a block game and have no regret at shooting people in the face or hitting them with a baseball bat. The game also is supported by Steam and has a workshop and community that I believe still works on cool community made projects. I currently have a single-player area that I picked up from the workshop of fighting on an aircraft.

This game is a gem and should get a lot more praise then it already does, for supporting people with anger problems.
Bro: WTF, My girl just cheated on me I'm going to kill a fucking dude!!!

Me: woah woah woah, it's okay... play Paint the Town Red

Bro: What the fuck does that have to do with anything about me getting FUCKING CHEATED ON!

Me: it's game where you can literally beat people up you should totally play that instead of actual violence.

Bro: your a fucking dumbass this is literally why no bitches talk to you
by Lol!po April 24, 2022
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'Paint the town red' is when I said what I said and I would rather be famous instead. It also can be used for when I let all the get to my head xxx<3
'CAROL YOU KILLED HER'
'Idc I paint the town red'
by Slay what you wanna slay September 24, 2023
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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 21, 2017
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