Well, it's hard for a woman to tell if he's homeless or not. Let's be frank, men smell, beneath that cologne they still smell. Some chics dig that scruffy homeless look...
The other day there was a chap literally wearing a soiled rag, very hairy like a neanderthal, maybe mid-30s, something seductive about it. So naturally I shuffled in my bag for some coins and placed it in his tattered cup.