He wants his sister to show him a picture of her friend so that he can propose to her
Question

A young man wants to marry his sister’s friend, and he asked his sister to show him her picture because he wants to see her hair, and he is insisting on that. Please note that he is a religiously-committed young man and he really wants to get married and not play about. He chose this girl because he knows of her good character, but he does not know how she looks, and he does not want to approach her family and conclude the matter before seeing her, because he may not like how she looks after concluding the matter and that would hurt her feelings. Can his sister show him a picture of her without hijab, without the other girl knowing about it?
Praise be to Allah.The basic principle regarding one who wants to propose to a woman is that he should look at her directly, not look at her picture. In the answer to question no. 4027 , we quoted from Shaykh Muhammad ibn ‘Uthaymin (may Allah have mercy on him) that it is not allowed to send the woman’s picture to the suitor, and he mentioned some of the negative consequences that are likely to result from that. But it seems that there is little risk of these negative consequences in a case such as yours, so there is nothing wrong with you looking at her picture, because if it is permissible for you to see her directly, then it is more appropriate to say that it is permissible for you to see her picture. But it is essential to pay attention to the following conditions and guidelines:
1. You should definitely intend to propose marriage. If you are hesitant, it is not permissible for you to look at her or at her picture, because Islam has only permitted looking for the suitor.
2. What should be visible in the picture is the woman’s face and hands, and what would normally be uncovered in front of her mahrams, such as the head and neck, because that is the limit of what it is permissible for the suitor to see of the woman to whom he is proposing.
If anything more than that is visible in the picture, it is not permissible for you to look at it.
3. Your seeing the picture should be through a trustworthy intermediary. It is not permissible for the woman to send her picture to the suitor so that he can see it, because of the negative consequences that may result from that.
4. The matter should be limited to seeing the picture only, and there is nothing wrong with looking repeatedly at it, but it is not permissible for the suitor to keep this picture, and it is not permissible for the intermediary to allow him to do that.
5. No man other than the suitor should see this picture.
With regard to the suitor seeing the woman or her picture it is not stipulated that the girl should give her permission.
Nevertheless, looking directly at the woman remains the basic principle, and it is what is preferred, because a picture does not really show reality as it is, in many cases.
And Allah knows best.