I read a bit of the webcomic Sunstone a few years ago and it was the first thing that sprang to mind when I read your post. ~ I recall that at least the beginning of the relationship was on the sweetly awkward side.
I also wonder if any of the Sarah Waters books might satisfy? (I've got Fingersmith on my kindle but not yet read).
The relationship of Exoristos (lesbian Amazon) and Sir Ystin (transgender man) in Demon Knights was complex and awkward and lovely (and there's been some good fic written about it).
(I do think, hands down, my favorite "female courts male and wins him" is probably Jadzia Dax and Worf from DS9 (but them I adore all things Dax. *g*)... and though she's not really awkward, courting a Klingon male does require fairly grand gestures.
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I also wonder if any of the Sarah Waters books might satisfy? (I've got Fingersmith on my kindle but not yet read).
The relationship of Exoristos (lesbian Amazon) and Sir Ystin (transgender man) in Demon Knights was complex and awkward and lovely (and there's been some good fic written about it).
(I do think, hands down, my favorite "female courts male and wins him" is probably Jadzia Dax and Worf from DS9 (but them I adore all things Dax. *g*)... and though she's not really awkward, courting a Klingon male does require fairly grand gestures.