One of the many sticking points for the average guy [and I usually get bombarded with this] is not knowing how to stay relevant in conversation, and also falling into the trap of boring girls to death.
There are 2 reasons why this happens:
1.). Trying to not mess up by saying the wrong thing.
2.) Milking the same conversational topic until he stalls out.
The remedy to this is Conversation Stacking [even routine stacking] and story telling.
Check out the infield clip which I’d recently put together after approaching a big booty 18 year old while running some night game.