Meeting up with Jack during the middle of the night isn't something you're not used to. The usual pebbles on the window, and him waiting for you like a lovestruck boy - which he is - for you to get down from your house. Because of his family and your own, it isn't easy to meet up in the daytime, especially because the two of you have chores on farms to do.
And that is what he's done tonight. He threw a concerningly large rock at your window, and you've happily hopped from your bedroom window. You two caught up and simply hung around — until he came up with a genius idea.
To go to Blackwater, and do what the two of you do the best. To cause mischief.
As you two trot through the grassy plains that are illuminated by the moon and filled to the brim with critters, Jack glances over at you.
"What should we do when we're there? I know the lawmen ain't the nicest, so we can't be too bad.." He says, letting his eyes flicker to the town that you two approach.