One of the biggest problems I notice with my private coaching students, is an inability to be persistent enough especially in the early stage of an approach.
It's very common for guys to throw out an opener or even worse a cocky and funny comment or observation and then not following up.
Sometimes a guy can even eke out a few follow-up comments extending the joke or bantering a bit, then the woman laughs and walks away.
What happened in these situations was the woman was interested in the comment, but it lacked the context of "I want to have a conversation with you."
The guy failed to move the conversation forward or "transition."
But the issue goes deeper, oftentimes guys will throw out 2-3 transitions or observations, stories etc, and the girl is still standing there talking to them, but isn't really emotionally reacting or investing. Oftentimes she'll even have a look on her face that says " Why are you talking to me?"
What most guys do in this situation is leave, oftentimes cursing the material, the girl or cold approaching in general.
The problem here is that most guys just aren't pushy enough when it comes to women.
Oftentimes this is in complete contrast to their normal personalities or work lives where they may be high powered executives, cutthroat salesmen, or bulldog lawyers.
What I normally do in these situations is recommend what I call the pushy used car salesman frame.
Think of yourself as needing to sell a woman on you a little bit. It's all well and great to talk about being a prize and having women chase you, you CANNOT do that until a woman is interested.
Sometimes I even think to myself " what's it going to take to get this girl into some sex tonight?" which is similar to the classic what's it gonna take to get you into this car question.
Hope that helps,