I was tempted to do a jerk playthrough when I first met Kenny and then immediately got yelled at for not moving fast enough to save his son. I could tell he was going to be a real pain in my ass the rest of the game, but I held strong and tried to react how I thought I would in such a situation, and Kenny turned out OK.
There were too many characters I liked, anyway, so I didn't want to be a jerk most of the time. Lily and Ben made me wish for more violent options in response to their actions, though.
I almost don't want to play through it again, because I've seen "my" story already, and I'm afraid it'll get too gamey if I'm choosing different answers just to see things turn out differently. It might be fun to watch someone else go through it for the first time.