"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).
On the phone one lonely Friday night...
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!
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!
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