I believe that the constant struggle with gender between the two characters may have been what sparked their love. Throughout the book Jake is constantly attempting to assure his masculinity. Because his injury in the war, he is struggling to find his manhood. In some ways that affects his gender, in turn, makes him want to feel more secure as a man. This I believe is where his relationship with Brett may come from. She is a woman, and Jake is no doubt aware of her feminine qualities. "She was built with curves like the hull of a racing yacht, and you missed none of it with that wool jersey." But, Brett is also a character who likes to play with her gender identity. A lot of the characteristics in Brett's appearance could be considered androgynous. Specifically her short hair cut, but also the things she wears. "She pulled her men's felt hat down and started for the bar." Additionally, Brett acts in a certain way that (20th century) society would not consider appropriate for a woman. One example is her relationship with many, and it seems mostly, men. Also her affection towards drinking.
Because of Jake's want for masculinity, I believe that Brett's masculine qualities appeal to him. I also think her confidence in her gender is also probably reassuring to Jake about his identity. Though the book may never mention these ideas, I do think they are worthwhile to explore.
I don't know--Jake seems pretty drawn to Brett's androgynous qualities. He mentions the "boyish" traits right alongside the more feminine ones as part of his appreciative appraisal of Brett's looks and style (and he also finds Romero androgynously "good looking"). And he seems pretty tolerant of her appropriation of masculine prerogatives of sexual promiscuity. It hurts him, for the reasons you've mentioned, but he doesn't seem to blame her for it the way Cohn and even Mike do. He seems to believe--or want to believe--that Brett would be different if she were in a relationship with him, but since she can't, she seeks sexual gratification elsewhere, and he's as okay with that as he is with his "rotten" fate more generally.
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