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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 03, 2011
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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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