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She should consider that the most important criteria for a good life partner is religion and manners. Weak religious commitments can lead to possible dangerous results in the life especially after few years. What can stop him in the future from looking for other affairs if his religious commitments are weak?

I don't advise her to marry a person who is weak in his faith and religious practice even if she has feelings and history with him. The feelings will never remain for long if there is no authenticity in faith and trust in religion.

Wassalam.

It is difficult to give recommendations without knowing the full circumstances of the case. It is advisable to get a senior scholar, or cleric, to meet with your parents and discuss the issue with them.

You may have heard the hadith that says that if a believer comes to ask for the hand of a young woman, and he is rejected for no Islamic reason, 'fitnah will spread on the earth.'

Cultural and family issues require sensitivity though. Your parents, and his parents need to be helped to overcome their fears. I knew of an English woman who married into a family and her mother-in-law initially threatened suicide, but after some years, all the other families in their community were saying that they wished they had a daughter-in-law like that English woman.

Bismihi ta'āla

Men and women, mahram or non-mahram, must always observe boundaries between each other. With mahram, the boundaries are less, but there still are boundaries. 

Most of what you have mentioned in your question is crossing the boundary, or should be avoided, so as to not all into haram. 

We cannot say he might have incestuous tendency, but it is not normal behaviour for a son to sleep right beside his mother and spend nights in her room, etc. He might have more feminine tendency, hence these activities, but it is also his mother to be responsible for this as well. 

I would advise someone have a talk with both of them, about boundaries, and the possible shaytani influence that could corrupt anyone.

And Allah knows best

Yes, post-menopausal woman does not require to observe Iddah after divorce or termination of a temporary marriage. This rule is only for those women who have no menstruation because of their passing the age of menstruation. This rule does not extend to women who had hysterectomy and no longer menstruate. Such women who are in the age of menstruation require Iddah.

It is worth mentioning that Iddah of Wafat after the death of the husband is obligatory on every wife. It is four months and ten days from her knowledge about his death.

Wassalam.