Board Thread:Speculation House/@comment-27121579-20151117081605/@comment-27124136-20151119155519

There's probably something approaching  legit rivalry between them. They knew each other before hand and Winter specifically mentioned that she has no time for Qrow's games, meaning he probably provokes her regularly enough for it to be a back and forth between the duo.

Add on top of that, Qrow seemingly being invested on waiting for Winter to show up means that he keeps at least somewhat of a tab on her.

It's probably a thing where the two fill out roles very similar to each other and constantly clash while doing the same mission