“The Man Trap” basically dispels the notion that Jim Kirk sees women only as conquests.
That first image – of a pretty blonde woman that looks uncannily like she’s from Wringley’s Pleasure Planet – is what a young crewman sees of “Nancy.”
The second is how McCoy remembers her, although she has by now considerably aged.
Jim sees her as she really would be.
Honestly, with only pop culture to go by, I would have thought Jim would react the same way the young crewman did. TOS taught me to know better – to not buy into the idea of James T. Kirk as a salacious playboy.
As for the bottom two pictures, they’re kind of unrelated to the topic at hand, I just like that Spock’s saving Jim! The first of many, many, many times!