An appropriate setting
When a woman is on her way to work, she is on her way to work. When she is grocery shopping, she is grocery shopping. When she’s at the gym, she’s at the gym. That’s literally all you know about her, and that’s not enough to gamble and put her in the weird situation of being hit on, just in case she’s super not into it.
There are times and places we just don’t want to deal with the male gaze, and we don’t want to socialize, but we have no choice but to be out in public near you. These examples are often among them.
Now I’m not saying I speak for all women in all situations, but in general if you’re not in a social setting then it’s best to assume it’s not the right time or place to openly hit on a woman. If someone does want to meet new people, they’ll go to social places, but if they don’t then they might still be at the store, gym or train station.
You have no way of knowing who’s feeling sociable and who isn’t in these places and for every woman who says they wouldn’t mind, there will be 10 others who don’t want the pressure.
Far better is to wait until you’re in the kind of places where meeting new people is the norm, like clubs, bars, parties, sporting events, shows and all those other very clearly social places.
The women you like might not be interested, but they’ve gone out to a place people go to when they want to socialize and have fun. That’s the bottom line.