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Islamically , Is it okay for a sister to let a brother (in islam) know that she cherishes him and she has the intention to get married to him? Is it considered to be bold approach?.
Praise be to Allah.
There is nothing wrong with a woman letting a man know that in principle, however the woman should not propose herself, rather it is better if that is done via her wali (guardian) or someone else who can let the man know. This is indicated by the fact that ‘Umar (may Allah be pleased with him) offered his daughter Hafsah in marriage to Abu Bakr and ‘Uthmaan (may Allah be pleased with them).