Manic Monday Triple Overtime--Would You Trust Your Daughter With James T. Kirk?!?

And then there was that time that Kirk totally hit on Dr. McCoy's daughter on while on shore leave:

Smooth, Jim...smooth!

Oops!!

Don't gloat yet, Bones...you can't keep Jim Kirk down long when there are lovely ladies involved, no matter whose daughter it is!

And Kirk pulls out all of his charm for Joanna:

Cue the soft jazz and fade to black...

The elder McCoy does not approve!

"Man of the galaxy." "He's been around." Oh, Bones, just call him a man-whore, why don't you!

Bones also lets Jim know that after years of urging on the captain's horndog act, it's suddenly no longer amusing:

Leonard McCoy: total shore leave block!

Well, after a harrowing adventure...

Yes, you go on believing that, Bones. You go right on believing that...I think we all know better.

20 years later, Kirk discovers another illegitimate child...?

From Star Trek: Untold Voyages #3 (1998)