Is it permissible for a suitor to sneak a look at his fiancée without her knowledge?

The questioner : My teacher, the way the looking is done with her knowledge, it will not be possible in this manner except in her home or in a safe place where no one sees her, right?

The Shaykh : I believe this has no relation to fiqh (Islamic jurisprudence); rather, it relates to the social situation in each country. For example, how did that Companion see her? He watched her and waited to see her while she was on her donkey on the roof of her house, hanging out her laundry. This is not something specific to that era alone, nor is it a fault to ask such a question about how he sees her. Seeing her now is much easier than in that time. (He laughs)

The questioner : The veiled, committed women, my teacher, it is difficult even to hang out laundry. Even if she is in her house, if she is uncovered, it is difficult for her to go out to hang it?

The Shaykh : That is what we want. (He laughs) But that does not require us to contradict the Shari'ah text. Yes, so how does he manage to see her without her knowledge? This matter is left to the skilled hunter. (He laughs)The Shaykh : May Allah have mercy on him.
Al-Halabi : Then there is a point. The question appears at the end as if it is a necessary, obligatory thing that he must see her, or how does he want to see her? If we do not see her in this manner, it is not a danger or a great error...

The Shaykh : This is a rukhsah (dispensation) in any case.
Al-Halabi : Yes, it is a rukhsah (dispensation) from this perspective...

Another questioner : And the point where I differed with you, my Shaykh, once in such a question is that you told me the mother should not convey it. Conveying is not permissible at all; but in this case, conveying is permissible. Your mother, your sister, your aunt, from the mahram (close relatives), regarding a description of her hair or her features...

The Shaykh : This is correct. This is established in the Sunnah that the Prophet (peace and blessings be upon him) proposed to a woman and said: And I do not know what?
Al-Halabi:

The Shaykh : Yes, so it is possible in another way that a man has a mother, especially if she is an old, skilled woman. They say in Syria, "a jinn," meaning she knows how to eat the shoulder and how to deceive with her mind, what? The fiancée. She approaches her and knows her height and weight, and so on. So this is one of the ways.