And then there was that time that Kirk totally hit on Dr. McCoy's daughter on while on shore leave:
The elder McCoy does not approve!
Bones also lets Jim know that after years of urging on the captain's horndog act, it's suddenly no longer amusing:
Well, after a harrowing adventure...
20 years later, Kirk discovers another illegitimate child...?
From Star Trek: Untold Voyages #3 (1998)