There's a difference between stopping to help someone whose gear cr@pped out, versus offering to help someone (still mobile) that just made a poor equipment choice.
Last week, I stopped on my way home to help some racer girl who flatted out on a training ride. I didn't have any spare tubes that would fit her gear since I ride a MTB, but I stopped to see if everything was OK... and it wasn't. She didn't know how to use her new CO2 inflator and managed to bust the stem on her only tube. (No spare, she'd just patched the one that flatted.) It was getting dark and cold, and she had no phone, so I let her use mine to call for a ride.
On the way in to work a few days later, there was the same guy I pass routinely: No reflectors, no lights, dark clothes, no helmet. It's his call to ride like that, and I don't feel obligated to slow down and help light his way. I'm sure that if he really wanted a light, he'd spend the $10 and get an inexpensive one.
In distress: I'll stop and help.
Just plain don't care: I don't care, either.
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"I feel like my world was classier before I found cyclocross."
- Mandi M.