We can't really judge your boss based on that. It is possible that he is just helping you to be at ease and taking you to those places is one of the things to do it. He may also want to let you feel that you can build a friendly relationship other than the professional. But we can't also take away the probabilty that this is another assessment that you have to undergo to prove yourself. But whatever his reasons are, you have to have a stand. Don't accompany him just to please him. It's a non-work related stuff and you still have the final say.
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