So, first topic:
1. “What makes a man the lady’s man?” aka Sexuality, looks and attraction.
A. On sexual attraction
It seems that it’s not required of men to look good in order to be attractive. Sure, there are some who are generally regarded as handsome (Renly, young Robert, Jaime, Loras) and this is a plus for them, until some doom takes away their looks (or life, in the case of Renly). Robert becomes fat, Loras is devastated and then crippled, Jaime looses a hand. And yet this does not remove genuine female interest in them. We have the prostitute in love with the new-old Robert, Cersei still wanting Jaime and Brienne being interested in Jaime. We haven’t seen Loras yet, but that’s probably going to be the case with him too. But moving the point even further, some men who are ugly from the start seem to find women with genuine interest in them: Sam with Gilly and Tyrion with Tysha are good examples.
However, Sam and Tyrion only get the girls after they have “proven” themselves “worthy”. Sam the fat coward never got the girl, but Sam the Slayer, Sam the Knight helping a damsel in distress did.
Tyrion the dwarf never got any attention from the girls either, but Tyrion the rescuer did.
Even the Hound, who is described as very scarred gets an un-Kiss for his knightly (oh, how he would despise this adjective) behavior with Sansa.
The conclusion is this: If a man wants to be attractive to women, he should be a knight. If he’s not, he’d sure as hell find a way to look like one, and find it fast, otherwise he is doomed. So while women need to be the Fair Maid, men need to play the counterpart and be the Just Knight. And while this stereotype is not what Sansa introduced us to with her early fantasies, it’s a stereotype nonetheless and one equally unrealistic to uphold.
This idea works on two levels – the first is the in-book experience. The characters in books seem to struggle with it and it harms them significantly.
But the other level is us, readers. We are equally exposed to this ideal. Why wasn’t Tysha a girl who liked the stories Tyrion told her? Why wasn’t Gilly in love with Sam, the nice person? Why is there a need for men to be “heroic” in order to get love?
B. On sexual pleasure
Men are not expected to and generally do not provide sexual satisfaction to the women they are with, and even our “good” guys are guilty of this. Cats “aching loins”, Dany “using her pillow to muffle her cries of pain”, than we have “Tyrion suspected her delight was feigned, but she did it so well that it did not matter” and many more. We have but a few examples of men providing pleasure to their partners. The first being LF with Lysa – we don’t really know what went on there, but she seemed to have enjoyed it. There is a hint that Jaime wasn’t so bad, Cersei said that it was only ever good with Jaime, but while we see her lust and longing, we don't really get to see her coming in their sex scenes.
Dany gets to like sex with Drogo eventually, but the first orgasm she achieves is with Irri.
Now the only two instants I recall of a female orgasm being described (disregarding the F/F scenes) are
The other is Jon and the Lord’s kiss:
Now it seems quite tragic that a woman belonging to the free folk, a woman who’s been sexually active for years, has no conception of what cunnilingus is.
But, as Jon states in the same chapter, he has no ideas what lords and ladies do in their castles. And how could he, or anyone else, since there’s no sex ed, no internet and this is not a lunch-time topic. So the only way for men to learn about sex is the way Tyrion and LF learned – women educated in the secrets of pleasure, provided that the men are interested in learning. This is quite tragic for the women in question, but is also the tragedy of Ned, Drogo and some others. It’s not necessarily the lack of interest in woman’s pleasure; it’s the complete sexual inadequacy to provide them with it. Since your wife (or a prostitute) is going to have sex with you anyways, there is no real need for a sexual connection. So women are learned not to expect it (“every man is beautiful in his way”) and demand it, and men aren’t learned that it exists beyond the “in-and-out” mode. This patriarchal structure, that robs women of the possibility to truly reject men and their sexual advances, also robs men of the possibility to provide a genuine, caring and satisfying sexual relationship.
Now in conclusion, I'm not saying that being a man in Westeros is generally terrible. But there are some very strong expectations and problems the men are facing, and they seem to reject and question them less than the women do. The very system that keeps them in power also seems to give them unrealistic expectations about themselves and it takes away one of the very few chances for something nice in a chaotic, ugly world they live in.
So, do you believe this structure harms men? In what ways? Am I being unjust calling the majority of Westeros men sexually inadequate? What defines an attractive man in Westeros?