If he's the type to usually be witty/funny and joking around, what things might he do around or how might he act differently with a girl that he likes? Or will he just act the same way with all girls?
The thing is if he has experience then you will not know. You may think he's a funny guy now and like that, but over time if he doesn't stop and get serious that humor will quickly turn to annoyance and frustration. It depends on how he is being funny. Some comedians and jokester's act that way to hide some issues.
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