DY -First of all, there is a common misconception that you are not allowed to reask a sheilah. That’s not true. (Don’t worry; I ‘ve asked a sheilah about this). If you are asking if a chicken is kosher, it may be different, because once a Rav poskens that it’s treif, I think it becomes treif even if the Rav made a mistake.
But most sheilahs don’t work that way, and if you have a reason to believe the Rav made a mistake, you should ask again.
The question is why you’re reasking the sheilah. If you are reasking because you think that the first Rav made a mistake, then you are allowed to (and maybe should) ask again. There can be many reasons why the Rav may be mistaken.
I had a situation once in which I realized that the Rav was wrong, not because he was lacking technical halachic knowledge, but because it was the type of halachic question that involves an understanding of the person, and he couldn’t relate to me or my situation.
I found out/realized afterwards that while this particular Rav is a tremendous Talmid Chacham and well-respected Poseik, he is not the best Poseik for me to ask halachic questions that necessitate an understanding of people’s emotions. On the other hand, he is a great person to ask sheilahs to when it’s a sheilah in which being less “emotional” is a maaleh.
I had another experience in which I called a halachic hotline, and it was clear that the Rav ( I don’t even know who it was, because they always have different people answering) did not understand the situation. When I tried to reexplain it, he cut me off. In that case, I also realized that I needed to speak to a Rav who I know I could explain the situation to, so I called a Rav who knows me and who was able to understand the situation.
On the other hand, if someone is reasking just because they don’t “like” the answer as opposed to feeling like the Rav didn’t understand their situation, and they make a habit of always looking for the Rav who will give the most meikel answer for each question, that is called “heter shopping”.
As I said, it can be a “thin line” and you have to know yourself and know why you are reasking the sheilah. If you know that you don’t always look for the “most meikel” answer, then there is a good chance that you are not “heter shopping.”
In this case, the reason why it seemed to me that it makes sense to ask another Rav is because it sounds like he is going through a difficult time and he needs to ask the sheilah to a Rav who will understand that and answer him accordingly. If he asks the “right Rav”, even if he does tell him to be machmir, it seems to me that ideally he should answer him in such a way that he will come away feeling happy that he asked and feeling better about the situation, which does not seem to have happened here. He also said that the first Rav didn’t even give him a psak, so there really shouldn’t be an issue here with reasking.
However, if he or anyone else is concerned that they should not be asking again, they can always play it safe by telling the second Rav that they already asked and tell him what the answer was.