It simply means that he is assessing you to see whether you would fit his definition of someone that he could ask out to be intimate with. He is basically checking you out to see your reactions and whether you are jailbait or not.
To me, that is the behavior of a player and I would be very cautious not to play his game if you don't want to get into trouble or simply be yet another number on his body count or trophy list.
Most Helpful Opinions
Well sounds frieny might have smashed you if you were closer to him.
Big difference between 19 and 25 emotionally!
Now he wants you to help others there and be nice and sweet. Just not to the point it hurts you.
He's interested and wanted to make sure you aren't underage
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