I once owned a business at the southwest corner of Shepherd and Alabama, and lived on West Grey. That was many years ago, however today...
If you want to see a half-undressed male of suspect gender-interest brandishing a machete like a fireworks sparkler and defiantly challenging the fire hydrant on the corner, well, Montrose is the place to be.
"Quirk" would be the kindest description of some of the Montrose residents. Not to say that many aren't affluent and upscale. Being near downtown, folks with big bucks have spent fortunes buying and renovating Montrose properties over the past several years.
The OP made it sound as if he were living simultaneously in a constantly-dangerous urban Ward and a pristine suburb where he could never imagine a guy coming up to him and asking a question.
The OP is obviously young, lacks experience, and has lived in that neighborhood only a short time. I'll repeat "lacks experience."
I rest my case.Ever since the previous night, all my weapons have been loaded, chambered, with the safety off.