I don't think your problem is lack of material.
I think your problem is transitioning from one topic to another. If you say 1 thing that is interesting, she will think - "Wow
that is interesting." If you say 10 things that are interesting, she will think "Wow,
he is interesting!"
You need to be able to relate any topic being discussed to something in your life or use it to find something about
her life. If you can't, then transition the conversation to something you
can talk about that will best convey your personality.
I suggest that you watch some comedians perform. Don't watch like usual, listen for how the comedian transitions from one topic to another - it's an excellent technique for keeping conversations going even when you run out of routines.
Notice how I said "
when you run out of routines," not "
If you run out of routines." Because sooner or later, you will have to (and want to) turn off game and it will just be you and her in comfort, when you can really show her your personality and have her like you for
you. At this point, she
will be interested, and she now has to work on keeping
your attention.
In general, socializing is like building a house. At some point, you will start building the house using routines and gambits as
tools, instead of using them as the
wood.
