The bar scene: "I just am having a hard time seeing Kirk as a whiny loser trying to pick up Uhura in a bar. I can't accept it. I just can't."
He was a dour, too-serious type when younger - if that's him being a "whiny loser," it's just following canon. It was only when he was older that he started to loosen up and gain the self-confidence not to be so stiff.
And I've always thought there was a nice sibling-like relationship between Kirk and Uhura. He was a bit like her big brother, always looking out for her and encouraging her when she needed it. For them to have some awkward but funny-in-retrospect first encounter wouldn't be too far fetched at all.