Wa ‘Alaikum Salaam sister,
Seeking a spouse can be a source of great confusion and frustration for so many people fo so many reason. Istikhara is always a recommended act to perform in such situations, so you are going about it in the right way.
There are some other points, however, that you must keep in mind as well. There is no limit to how many times you can perform istikhara, but be aware, there is no evidence to suggest that the answer will come in a dream as istikhara is simply a prayer for Allah’s (swt) guidance. To make istikhara, you are asking Allah (swt) to guide you. This might not necessarily be through a dream, but in the way you feel, the actions you do and opportunities that become available or unavailable to you.
You also need to be careful about the time you spend with him for a number of reasons. Firstly, it is not permissible to be alone with him because we know it’s said that when a man and woman are alone together then shaytan is the third person and may plant ideas in your head or, in the worst case scenario, lead you to commit acts of serious zina. The other thing is that, being with this man is also going to result in developing feelings for him which you might mistake for Allah (swt) answering your istikhara with a positive answer to pursue marriage to him, when actually these feelings have developed because of spending so much time with him. These are things to keep in mind when making istikhara and interpreting what the result of your prayers are. Your feelings that you have developed towards him will also be tainting your opinions on whether any of the suitors that your mum finds for you are right for you, because in your mind, it seems that you have already decided that this other man is the one for you.
I certainly can’t advise you to go ahead and tell this man directly what’s happening is not permissible in Islam, but if you reflect on my words regarding how the time you have spent together may influence you heart, your decision, and your interpretation of your istikhara and still decide that he is the one for you, then it is important that you go ahead in the most permissible way. You can either approach his family, or have someone from your family to approach himself or his family to move forward with a proposal.
If you feel that the time you have spent with this man may have influenced your thoughts and you chose to leave this as an option, and instead seek a spouse with the assistance of your mum, keep in mind that your mum is wiser than you in marriage and only wants to look out for your best interests. So, give other potential suitors a chance also. Your mum has a more neutral position on the matter so is in a good place to advise. So try to be more open minded about the potential for another spouse. She is going about it in the correct way and organise meetings in a halal way to pursue other options.
May Allah (swt) bring a suitable spouse your way that you will be happy and content with. May He (swt) bring happiness and contentment in your lives in this life and the next.
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