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Rav Kook says in his perush on the siddur, Olat Rayah, that we ask Hashem to save us from a chaver ra after already asking Him to save us from a bad person because sometimes when two good people get together (mitchabrim) there is a bad result. This, Rav Kook says, is connected to the secret of neshamot that Hashem keeps to himself. I think that the same applies to choosing a rebbe. You come acrosss a rav with whom you feel a good kesher. Whether you choose him because of his hashkafa or choose your hashkafa because of him is probably a chicken-and-the-egg question unless you are very young. As for confiding, this is dependant on one’s personality. Some people tend to keep their own counsel, others confide in just about anyone and the rest are somewhere in the middle.