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a confident and adult obi-wan might well indulge in cultured-toned sexual innuendos, especially as he'd be quite comfortable with qui-gon. qui-gon would allow it and respond without being, shall we say, as inclined towards it himself. or perhaps he'd accept and enjoy it without really bantering back, or returning the sallies only infrequently. but he could be uncertain of the true meaning of the remarks, as could obi-wan. there would be such a constant level of affection in their bond (if this is pre-knighting that is), and they would be so careful and so given to second-guessing their judgement about such a touchy matter, that they could easily both be uncertain. although certainly not too much angst should be introduced. maybe a twinge or two, but jedi obviously don't experience little teapot tempests of frustration.