Where's any evidence that the Farragut was lost/destroyed? The ship was attacked by the Space Vampire Cloud which killed half its crew, including the Captain. The Space Vampire Cloud showed no capability to destroy stuff, only suck the red blood corpuscles out of people. The other half of the ship's crew had to get home somehow, most likely on the Farragut. ~10 years later in SNW, the Farragut looked fine to me (at least until Kirk destroyed it).Was not the Farragut supposed to have been lost in 2257, which would not fit with the new shows?

Ya, I was exaggerating things a bit to introduce my new "Kirk drift" idea that he wrecks ships. More honorably, Kirk could have gotten a plumb assignment at Starfleet Command.That's a big stretch, IMHO.
As to why I like to put Kirk on a ground/base assignment, it gives a one year time window for Lester and Kirk to establish a close relationship which I don't think could occur if Kirk is ship based and Lester wasn't. Then again, Kirk and Lester could be on the same ship, but I like this less likely especially if Kirk is either commander of the ship or its first officer, hence the idea of a non-ship assignment. Repeating myself from before, I decided to put Lester later in Kirk's timeline simply because of the "your world of starship captains..." which as the only clue, seems to link Kirk to getting promoted to Captain of a starship, and hence, shortly before he gets the Enterprise. Any other time is just as good, but with less evidence IMHO.
Back to the original Kirk drift on womanizing, here's my order of Kirk's pre-TOS girlfriends covered in the series:
- Ruth
- Carol Marcus
- Janet Wallace
- Areel Shaw
- Janice Lester
- USS Enterprise
- Helen Johansson? <Could Helen Johansson actually be Helen Noel after she left the Enterprise and got married?>
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