Ruling on seeing the woman one wants to propose to more than once, and sitting with her
Question

I proposed marriage to a woman, but when I saw her she was very shy, to the extent that I could not see her face because she was so shy. Question 1: is it permissible for me to ask the family of the woman to let me see her and sit and talk to her before completing the agreement and getting engaged? 2. Is it permissible to pray istikharah regarding more than one woman, meaning that I saw two girls for the purpose of marriage, and I like both of them, but I need to pray istikharah to decide which of them is best for me? 3. How should I choose a wife, from the point of view of beauty, lineage and religious commitment?
Praise be to Allah.Firstly:
It is permissible for the suitor to look at the woman to whom he wants to propose marriage, and sit with her and talk to her, even if that happens more than once, so long as he is undecided and his aim is to reach a definitive conclusion, and make sure that both parties are happy to proceed with the marriage. However, it is stipulated that this should take place without them being alone together, and that any conversation is limited to permissible and regular topics.
Once he has decided to go ahead with the proposal or not, then the ruling reverts to the original, which is that it is prohibited to look at her, because the reason for it being permitted no longer applies.
This is indicated by the words of the Prophet (blessings and peace of Allah be upon him): “If one of you proposes to a woman, then if he is able to see that which will encourage him to go ahead and marry her, let him do so.” Narrated by Abu Dawud (2082); classed as hasan by al-Hafiz Ibn Hajar in Fath al-Bari (9/181).
Shaykh Ibn ‘Uthaymin (may Allah have mercy on him) said: It is permissible to look at her repeatedly… If on the first occasion he did not find anything that would encourage him to marry her, he may look a second time and a third. "(Ash-Sharh al-Mumti‘  12/21).
Shaykh Ibn Baz (may Allah have mercy on him) said: It is permissible for a man, if he wants to propose to a woman, to speak to her and look at her, without being alone with her… And if his conversation with her is to do with marriage, housing and her character, to find out whether she knows about such and such, then there is nothing wrong with that, if he wants to propose to her."(Majmu‘ al-Fatawa  20/429).
In al-Mawsu‘ah al-Fiqhiyyah (22/17) it says: It is permissible to look repeatedly, if need be, to find out how she looks, so that he will not have any regrets after marriage, because usually this purpose is not achieved with the first glance.
Please see the answer to question no. 13791 .
Secondly:
The basic principle regarding istikharah prayer is that it has to do with one matter, which the person may either do or not do.
Therefore you must decide and choose one of the two options, then pray istikharah based on that choice, and go ahead with the matter. Then if it does not work out for you, then you may pray istikharah again about the second girl, and so on.
If you pray istikharah separately for each girl, there is nothing wrong with that. Please see the answer to question no. 130169 .
Thirdly:
The Sunnah describes the characteristics of the woman whom a man should be keen to marry, which may be summed up as follows: she should be a virgin, religiously committed, of good lineage, beautiful, and wealthy. That is because the Prophet (blessings and peace of Allah be upon him) said: “Women may be married for four things: their wealth, their lineage, their beauty and their religious commitment. Choose the one who is religiously-committed, may your hands be rubbed with dust (i.e., may you prosper).” Narrated by al-Bukhari (4802) and Muslim (1466).
If the woman has all of these qualities, then that is even better, otherwise you should give priority to the most important of them, and the most important of them is that she should be religiously committed and righteous, as the Prophet (blessings and peace of Allah be upon him) said: “This world is no more than temporary joys, and the best temporary joy of this world is a righteous wife.” Narrated by Muslim (1467).
It was narrated that Abu Hurayrah (may Allah be pleased with him) said: It was said to the Messenger of Allah (blessings and peace of Allah be upon him): Which kind of woman is best?
He said: “The one who makes (her husband) happy when he looks at her, obeys him when he tells her to do something, and does not disobey him with regard to herself or her wealth in a way that he dislikes.” Narrated by an-Nasa’i (7373); classed as hasan by al-Albani in as-Silsilah as-Sahihah (1838).
See also the answers to questions no. 72255 , 125907 ,and 96584 .
And Allah knows best.