I will go back and look at it. This has been one of my main complaints since the last time that I played. My experience has been what RenH described. If it is possible to be approached, I will try it again, but really it should be a default setting if so.
No I reloaded the game, got all pretty and attractive, went to clubs, the park, the mall, everywhere I knew of, and the only "approaches" are scripted events where for instance a drug dealer will try to sell you drugs. If you say no, it will never repeat again, and never has any npc approached any of my characters romantically. Again, it's really not anything even vaguely resembling most women's social interactions. It could only work for one who is 100% proactive all the time.
I made my character "approachable" too. It's just I think it is actually impossible to be approached in the city itself or in an open world building.