At the end of Balance of Terror Kirk mourns with a junior female officer at the loss of her fiance, a junior weapons officer. Kirk had been in the process of marrying them when the episode began. I understand that this is an exception to the red-shirt rule, in which Kirk willl deliver a few testy lines "a member of my crew is dead!" before moving on, but it's worth noting in context of Picard 'thank you very much, moving on' attitude at the end of Generations.
"Yes, the Enterprise
just got destroyed under your command, Number One...and...oh, yeah...Captain Kirk's buried right over there under some rocks. Long story. Anyway. WHO WANTS NACHOS??