From my observations regarding Kirk and women, I think the only two females Kirk fell in love with were Edith Keeler (City of the Edge of Forever
) and Miramanee (The Paradise Syndrome
All the others were strategic moves by the good captain. If a man got between Kirk and the Enterprise
, he'd knock him out. But if a women came between the captain and his ship, Kirk tried a kinder, gentler approach. And if that didn't work, the captain knocked her out (equal opportunity and all that).
There's a telling scene in "The Mark of Gideon" when Odona interrupts Kirk's flirtations by stating he must be worried about the rest of his crew since they're nowhere to be found on the Enterprise
. Shatner's face changes from "come hither" to an expression of anger, then back to the look before.
I always thought that explained a lot about Kirk's "womanizing." It was a strategy, not an attempt to take his boots off. But hey, that's just me....