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Do you think that one needs to ask his Rebbe all personal life questions like for example in this case if it is time to start shidduch dating, or should one decide this on their own? Real life question by the way.
Yes, ask. You can’t go wrong. And he is wiser (and a bigger talmid chochom) than you.
I think someone must ask a rav any question where they think it is a question of what G-d wants them to do, and they are not sure themselves. (How do you know if you are sure? If you are afraid your rav will disagree, then you are unsure.)
Things which are not a question of what G-d wants, but just questions of what you want, can be asked to your therapist. But if you like to ask your rav because you think he is wise–go for it.
If he is really your Rebbi, ask. You will get sagacious advice and his heartfelt Tfillah as a side benefit. It also helps if you run into problems, he is connected with the matzav and can provide more comprehensive direction.
In addition, sometimes you don’t see a second side to an issue anad he may see a few more. Why not utilize your resource? If you were investing $$$$ and you thought maybe reuvain has some possible info about the company, you’d call …… call your Rebbi!
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