Yeah, he did.
And when he asked Kagura something along the lines of, 'What you hate more, teaming up with me, or beating the enemy?', and when Kagura said 'Both', he seemed to consider it for a moment before stating, 'Yeah, me too.'
And of course, there's all their little fights, like at the Sakura viewing party, when they went to that festival, when they were investigating the ghost at Shinsengumi headquarters~ then Shinpachi remarked, 'Why do you two always have to fight?'.
And then there's one of my favorite episodes~ the beetle catching one. The whole episode is basically based around them, with Kagura doing so much to get her back on him that she'd make herself throw up over the barbecue. The look on both of their faces was hilarious, both basically saying, 'Bring it on'.
When Sougo was on his own in the tree, he said something like, 'That China, eh?', and he seemed to be considering her.
In regards to pairings and Shounen, it'd be incredibly silly of me to hope something comes out of it, but then again, you can see things between Otae and Kondo, Otae and Kyubei, and a few others, if you squint.
Perhaps it isn't that far fetched, after all.