This shows that he must not be alone with her, she should not know that he is observing her, and he may look only at that part of her body which ordinarily remains uncovered. This concession applies exclusively to the man who has good reason to think that his proposal will be accepted. If direct observation is not possible, he may send a trustworthy woman to look at her and then describe her to him, for it is related that “the Prophet, peace and blessings be upon him, sent Umm Sulaym to look at a woman,” reported by Ahmad.
If someone is asked for advice about a prospective suitor or bride, he must disclose any faults or other relevant matters he knows; doing so is not considered backbiting.
It is forbidden to make an explicit proposal to a woman who is in her waiting period, such as by saying, “I want to marry you,” because Allah the Exalted says, “And there is no blame upon you for that to which you [indirectly] allude concerning a proposal to women” (Quran 2:235). The verse permits indirect wording during the waiting period, for example: “Someone like you is certainly desirable to me,” or, “Do not deprive me of yourself.” This establishes the prohibition of explicit wording—such as “I want to marry you”—since explicit speech can mean nothing but marriage, and the woman might, out of eagerness, claim that her waiting period has ended before it truly has.
Imam Ibn al-Qayyim said: “An explicit proposal to a woman in her waiting period is forbidden—even during the waiting period of widowhood—even though determining its end is not in the woman’s hands. Allowing proposals could be a means that leads her to hasten in responding or to lie about the completion of her ʿidda. An explicit or implicit proposal is, however, permissible for the man who issued her an irrevocable divorce, without…"