I remember there were some interactions between the two in Final Frontier, but for the life of me I can't remember the specifics.

I do remember the two coordinating as, what would appear to be, fairly close friends in Undiscovered Country though, which I think felt appropriate. It was subtle enough that you could tell that the two were closer, but it wasn't clear if it was due to past or present romantic developments or just some other friendship building events events between the scope of the two films. The end result at least in that film felt natural.