SO yeah, I think it depends on the Lady.
How and who I approach is determined by the signals I get. The more overt signals I get, the more cautious I get. The more subtle and playful signals I get the more forward I'm going to be.
Like if I girl asks me out and tells me how much she likes me, I'm probably going to ignore her for as long as my conscience will let me. Its like saying, "Hi, I'm dumb and don't know what I'm doing but, you look shiny."
But if a girl argues with me, flirts with me, gives me *the look* or challenges me, I will more than likely pursue her. That says, "I'm a passionate person, if you want me, prove to me that you are my equal, come and claim me."