Praise be to Allah.
The Messenger (blessings and peace of Allah be upon him) instructed the one who wants to propose marriage to a woman to look at her, and he described that as one of the means of creating affection between them.
At-Tirmidhi (1087) and Ibn Maajah (1865) narrated from al-Mugheerah ibn Shu‘bah (may Allah be pleased with him) that he proposed to a woman, and the Prophet (blessings and peace of Allah be upon him) said: “Go and look at her, for that is more likely to create affection between you” meaning that it is more likely to create lasting affection between you. This hadith was classed as sahih by al-Albani in Sahih at-Tirmidhi.
Abu Dawud (2082) narrated that Jabir ibn ‘Abdillah (may Allah be pleased with him) said: The Messenger of Allah (blessings and peace of Allah be upon him) said: “When one of you proposes to a woman, if he is able to see of her that which would encourage him to go ahead and marry her, then let him do so.” Classed as hasan by al-Albani in Sahih Abi Dawud.
The conditions of it being permissible to look at the woman are six:
- It should be without being alone with her.
- It should be without desire.
- He should think it most likely that they will accept his proposal.
- He should look at what usually appears, such as the face, hands, head and feet. As for anything more than that, it is not permissible for him to look at it.
- He should be serious in his intention to propose.
- This is addressed to the woman: she should not appear wearing make-up or perfume.
The wisdom behind the suitor looking at the woman to whom he wants to propose is that he may find out more about her, and propose to her when he is pleased with her, lest he see something in her after marriage that he dislikes, so he regrets marrying her.
Ash-Sharbini said in al-Iqna‘ (2/405): He may look repeatedly if he needs to, so that he will have a good idea about her appearance, and so that he will not have any regrets after marrying her. End quote.
As for asking a lot of questions about her hobbies and ambitions, and about shaykhs and scholars, and the like, what we think is that this comes under the heading of asking too much, for which there is no basis in Islamic teachings, and it was not the practice of the righteous or of people of prominence and dignity. Moreover, they may get carried away in their conversation, and the like, in addition to the fact that usually that has no great value in ordinary married life, and it does not reflect the situation precisely. Rather the suitor should try to ask about all that from acquaintances, relatives and intermediaries, before he proposes marriage, and getting carried away in talking is not praiseworthy in this situation.
Bu if he is concerned about a specific matter, he may ask about it so as to put his mind at rest, without asking too much.
It is not permissible for him to sit close to her, rather he should sit far away from her, but in such a manner as to be able to fulfil the purpose of seeing her. That is because she is still a stranger to him, and Islam has only granted him a concession allowing him to look at her so that he will not have any regrets after marriage.
Rather he may sit with her until he is certain whether he would be pleased with her as a wife or not.
It is not permissible to laugh a great deal, or to speak softly or to speak at length about any unnecessary matters, and other such matters that are not permissible between a man and a woman who is a stranger to him.
You can learn more from the book Tuhfat al-‘Arus.
For more information on proposing marriage in the Islamically prescribed manner, please see the answer to question no. 88130 .
And Allah knows best.