As a Man: When to not try checking a woman
I lay no claim to expertise or even competence at approaching a woman, expressing in no uncertain terms that I am interested in a connection that may include friendship but is not limited to that. It has always been my view that these things develop organically - boy and girl meet while pursuing a mutual interest; boy and girl like each other and things develop from there.
Based on what I have seen, though, I can definitely say there are a few circumstances under which a man should not try to obviously check a woman for possible mating.
Top of the list is when she is with her child or children. It is something I have seen enough to know that it is at least disturbing and more often outright disgusting. A woman is walking with her offspring, who are old enough to understand the conversation. Here comes some crude fellow who comments on her physical appearance then attempts to strike up a conversation to spark her interest and see her another time.
To her children, this woman is a mother, an authority figure. How the heck does he expect her to react when he tries to treat her overtly as a sexual being in front of the little ones she needs to have the respect of? Not that being Mommy and being sexy are mutually exclusive - they go together wonderfully.
But making that explicit initial contact while the children are around is downright sleazy.
Another circumstance in which it is tacky for a man to try hooking up with a woman is when he has just done something to help her. It could be stopping and helping out with a flat tyre, or cutting her waiting time in the tax office. If the relationship is established from the get-go as, 'I do something for you, you do something for me', the only thing that can happen is that the rate will go up. Sure, many women call the shots in this kind of arrangement, putting a price on the business, in the land of 'pay dung pon it', as Shabba Ranks once deejayed. But there are exceptions to this matter of trading titillation.
AFTER A WORKOUT
One last situation in which a man should not approach a woman for a possible sexual relationship is when she is finishing a workout (gym, martial arts, jogging, cycling, etc), unless he was part of the physical exertion. The clothes tend to be all clingy in the first place, and the sweat makes it even more form-fitting. This makes it more appealing to the male onlooker, but the woman who has just been through the exertion (and I am not talking about the workout posers) is sure as hell not feeling her sexiest. But here comes a man who has not been through the pain and stress of the exercise, saying, "Waapen baby, yu look sweet."
Chances are the conversation is going to go downhill from there.