What the hell happened to being polite? If you are out on the street and see a woman with headphones smile and leave her alone. (A smile is polite a leer is not.) If she smiles back then just as you are about to pass her look back. If she also looks back then make the gesture to get into a conversation. There is a connection. You have given her the choice — and the woman’s choice should be respected.
Otherwise…when you pass her leave her alone and be a gentleman.