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I can totally feel that man, I think a lot of us are like that or at least have been at one stage! It just improves with practice I think, best thing to do is REFLECT on what you did and what you could have done, and that will all build up in your mind and start coming out more naturally. Chances are you have the ability to come up with heaps of awesome and fun stuff, it's just a bit hard when you're not completely comfortable yet.
Yeah I suppose it's just practice

In my opinion it's the difference between a girl that's neutral about seeing you again (oh he's a nice and cute guy) and a girl that's excited about seeing you again (omg he's funny and I like him).
Oh well, practice practice here I come!