|For the color one, I shot him from far away....he seemed to be lost in thought...just staring off into the distance, so I didn't bother him.
On the b/w one, I approached him and asked. He wanted a cigarette, but unfortunately I was out, so I gave him a dollar. (I had already dropped a handful of change in his cup when I approached him.)
Unless I want to get a shot of the person looking at the camera, I usually don't ask because I tend to shoot from far away....I like to get natural unposed shots. (Unless, of course, it's something I think I'll want to use "commercially". I do carry model releases with me, just in case.)