Why didn't Pless take the guide?
He needed to take a break. And by "take a break," Kenjiro usually means doing something worthwhile, not just wandering around entertainment venues. Although right now, he would gladly give up half of his earnings for a jug of sake while listening to the soothing sounds of a shamisen, in good company...
And yet, there are better and more important things to do right now. Either go watch the arena, or go talk about that tournament. There probably aren't any fights at the arena at night, but you can at least find out about upcoming battles. As for the tournament... it's better to do that tomorrow. With a clear head, and Klin can help with information.
Kenjiro goes to the arena.