Hanging out 'Entourage'-style.

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Hi,

I have a very great difficulty in just chilling around with friends. It's very hard for me to get at it.

It seems like I build a scenario of my day-to-come every morning and then act as if it's set in stone.
When I look at NT friends, they can just say 'f**k it, let's go have a beer in the park in ten minutes'.
Or just hang out with each other all day, playing some games here and there, watching tv or whatever. (hence the use of Entourage-style in topic)

I know I like doing this, from the few moments it truly worked out. I have friends who like it and ask me sometimes.
But I always kind of flip and say 'no' immediately because I don't know what to do.

What could you suggest me to try so I can get a good shot at this? Do you guys do this? Do you like it?