Jack was worn down. The city was getting to him again, and frankly he didn't know how his two slayer friends handled it. Well one slayer friend. The other one was busy getting drunk and flying off the handle. He was surprised he wasn't right there with her since Charlie was in town. Since the Angel thing fell through. All their work down the drain. It was enough to break a person. It was at least the fourth night, severe worry was eating at him, apathy settling in it's place instead.
Kira needed a break from him. From Sam, it wasn't exactly what he wanted to hear. It didn't exactly make him feel loved. He wondered what was going through her head when she was doing this. Or rather not going through it. She knew Charlie was out there, she knew he had many enemies, and probably a few of her own. He was less than thrilled to be in a club, even if Kira was headlining. He knew she was. She had to be. "Lets get this over with." He said to the younger Winchester with a half smile and a roll of his eyes as he settled at the bar to watch the stage.