When I started approaching I approached literally everyone. Any time I was in the presence of someone for more than a few seconds I would initiate conversation, regardless of their sex/race/age/etc. This improved my conversation and rambling skills immensely, as well as introduced me to new females, made me some interesting and beneficial new friends (the middle eastern guy at the store near my house no longer charges me debit transaction fees) and gave me a few interesting stories to use in future conversations. I now start conversations with everyone around me (including females) without conscious effort. I chatted up a pair of old women yesterday on my walk home; we talked about the weather, then I brought up that I'm glad it's going to rain this weekend because I need to study for final exams. I learned from one of the old ladies that her granddaughter just graduated high school and is moving down here in a few months for college (score!)
Consider that, even if you feel like you are already a strong conversationalist. (Hint: your not if you don't know how to approach.)
Edit: also, don't eliminate the possibility of getting "action" out of your approaches, even approach number one. Could result in a self fulfilling prophecy. Go into the conversation with the intent of the lay (if applicable,) but don't overvalue it.
Consider that, even if you feel like you are already a strong conversationalist. (Hint: your not if you don't know how to approach.)
Edit: also, don't eliminate the possibility of getting "action" out of your approaches, even approach number one. Could result in a self fulfilling prophecy. Go into the conversation with the intent of the lay (if applicable,) but don't overvalue it.