I am finishing, with G-d's help, in a few weeks a compilation of sources dealing with gender, sexuality and marriage. These are taken from the sefer.
Igros Moshe (E.H. 04:060): Concerning the issue of a young man who is not ready to get married and has no interest in getting married and he is interested in having social dates with young women who also are not ready to get married and have no interest in getting married. They say that since they are careful to avoid the prohibition of yichud (seclusion) there is no prohibition in dating. Even though they know that this is not nice but they say they are not interested in issues of piety and extra measures of modesty and they don’t want to listen to lectures of mussar and rebuke. However they say that they will stop if they hear from me that this is prohibited according to the halacha. Therefore I am forced to respond immediately because this applies to a current activity… There is also a severe prohibition from the Torah in close friendships between a young man and woman. That is even if they avoid hugging and kissing as well as touching and yichud. The problem is that he talks with her for extended times in expressing love and he gets pleasure from this and stares at her. Even according to the Ramban who disagrees with the Rambam and holds this is only a rabbinic prohibition nevertheless agrees that this is a severe prohibition since it has an asmachta from a verse and that it is punished with rabbinic flogging. It is clear that dating is done because of love of women and not because of ordinary friendship since he clearly prefers being with a woman then with male friends. Why is he interested in this woman when it doesn’t give him greater respect or a good name? It is obviously because of love of a woman because she is a woman. In addition even though she is unmarried, she is a nidah which is prohibited with the punishment of kares…
Igros Moshe (E.H. 04:066) Is there a concern with hugging and kissing wife for wasting seed (zera levatala)? Regarding the issue of hugging and kissing one’s wife when she is not a nida - is this permitted to him. Your brother has mentioned to you what I said about this but you wanted that I put this issue in writing for you. It is explicitly permitted and sometimes even also a mitzva for someone who goes on a long trip just before his wife is assumed to be a nida. In such a situation, however, it is better to be strict and have sexual intercourse as is stated by the Rema (Y.D. 184:10). However he writes that all types of intimacy and love are permitted except for intercourse. The Shach writes that intercourse is also a mitzva. But I have previously written in Igros Moshe (E.H. 1 68) that this is permitted only when he is certain that there will be no emission of sperm. He can rely on that belief because he is used to his wife so he does not have to be concerned that this behavior will produce lustful thoughts that result in zera l’vatala. It is reasonable that if he doesn’t have an issue with zera l’vatala but his only concern is for an erection there is no prohibition. This can be seen from the Rambam (Issurei Bi’ah 21:09), A Man’s wife is permitted to him. He can have intercourse, naturally and unnaturally as long as there is no zera l’vatala. Without erection it is impossible to have intercourse and yet he says it is permitted to have an erection and even have unnatural intercourse as long as the husband does not produce zera because of it. Even though we don’t know that such is possible, but we see from the Rambam and many other authorities such as the initial view of Tosfos (Yevamos 34b) that there is such a possibility. It is obviously very rare but nevertheless it is appropriate to rely on them if one is confident there will not be zera. Consequently the reality of an erection is that it is clear according to everyone that there is not always spontaneous emission of zera even when the person had intention to have sexual intercourse. But if he didn’t have actual intercourse and didn’t stimulate himself and only got sexually aroused from thoughts there is not always emission of zera - as we see that even when there is a need for the emission of zera e.g. Yevamos (76a) that states that zera is not emitted solely by lustful thoughts alone in most men. … from all of this we can conclude that arousal which produces an erection does not typically produce zera when there is no intent for intercourse. Unless we are talking about staring at women he is not familiar with or their colored clothing that he is not accustomed to etc.- unless he is like Barzili HaGiladi for whom lustful thoughts was sufficient. Ordinary men do not emit zera in relation to their wife or colored clothing they are familiar with. Consequently everyone agrees that there is no concern for zera l’vatala when hugging and kissing his wife even if he becomes sexually aroused
Igros Moshe (Y.D. 01:137): Coeducation, for even the youngest children, is surely something that would not please our Sages. While small children experience neither temptation nor lewd thoughts, we must still train them to distance themselves from women. Yet when they study together, they become accustomed to closeness. They will remain accustomed to this when they grow up, as well, when they do face temptation, and the danger of lewd thought. Therefore, although there is no risk of breaking any prohibition now, our educational duty still stands." I am willing to be lenient in an emergency, where an all-girl school cannot be formed, and the alternative is public school." which teaches neither faith nor good deeds. Better that very young children, regarding whom the prohibition does not apply, should be educated in schools founded by the God-fearing, even if boys and girls study together. It is clear and simple that if there is any chance of founding an all-girl school, it must be done. Of course, slightly older children are legally forbidden'" to study either religious or secular subjects in such a school.
Igros Moshe (Y.D. 01:090): A boy and a girl want to get
to know each other for the purpose of marriage to determine whether they will
like each other. They want to know whether it is permitted to rent two separate
bedrooms in one house where the owner and his wife also live. It is clear that
if it is known to the owner and his wife that they are not husband and wife –
there is reason to be lenient. However if they have not informed then it is possible that they
might mistakenly assumed that they are married and therefore it won’t help that
the owner lives there. If the owner doesn’t know that they are not married it
would thus be prohibited to rent the separate rooms because the owner is no
longer a protection against sin because they are not embarrassed to be alone
together and other similar problems. Regarding the issue of whether it is
permitted for her to prepare meals for him, it seems that there is no concern
that this is prohibited according to all authorities. That is because this is
not included in the prohibition of utilizing a woman’s services. This type of
service is permitted as is serving as a maid – even if she does it for free.
All of this is permitted according to the strict letter of the law – however in
actuality it is not worth doing. A person shouldn’t try to be too “smart” in
these matters. It is sufficient if she finds favor in his eyes - regarding her
appearance, her family and her reputation concerning her religious observance -
that he can rely on that to get married with the hope that she was the one
designated for him from Heaven. It is not necessary to examine her first.
Furthermore this “test” is worthless to determine if she will be a good wife.
Rather the Torah tells us to be “tamim” (to have simple trust) with G‑d.
