In a knee jerk reaction, I lost the timeline about Mitchell's "little blonde lab technician" comment; yes, it happened later, after the
Farragut incident though I put their romance a little shorter; started in 2257 with David born in 2258 making him almost 25 in the
TWOK.
Also, I agree on the
TWOK 2283 date. Both Kirk and Khan say 15 years ago, so, that's gives 2268 for
Space Seed. I also have TOS Season One starting in Sept 2266 (Stardate 1329.1), and spanning two years (mostly because of the passage of almost two thousand Stardates) which puts
Space Seed in July 2268 (Stardate 3141.9). It fits! Also, the Stardate of TWOK is 8141.6, or almost exactly 5000 Stardates; add in a dropped 10,000 Stardates to keep the four digit format, and you get 15,000 Stardates or 15 years to the day. It fits, too.
As for Janice Lester, I have their one year romance more recently starting in 2264 then breaking up right before if not due to Kirk getting his promotion to Captain and being assigned the Enterprise. I fits better with Janice's "your world of starship captains...". She says, "Starfleet" and not Starfleet Academy. Perhaps Kirk had a ground posting job somewhere in Starfleet for the one year before getting the Enterprise in 2265. At least it fits. YMMV

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Seems like a perfectly valid interpretation of the facts to me. I agree with a lot of what you've concluded!
What is in Kirk’s TOS character bio is he commanded another ship before the Enterprise, and it’s backed up by Dehner’s reference to his first command in WNMHGB. Makes sense because you wouldn’t give command of one of your best ships to an inexperienced neophyte.
Yeah. I couldn't deny the logic of Kirk commanding a smaller ship before the
Enterprise, so
in my timeline I have him taking command of the USS
Saladin in 2263 while he's still at the rank of Commander. (Sorry I can't link to a specific year/section of the timeline, but Sutori doesn't work that way.) That way the
Enterprise can still occupy a special place in Kirk's heart, as it's his first command as a Captain. But I'm happy that I gave Kirk a much more realistic career progression than the has in the official Okuda timeline.
How did you decide on winter/fall timing and things like New Year's Even for a proposal?
Trek doesn't have a whole lot of definite dates, so I generally give characters the same birth dates as the actors who played them. Merritt Butrick was born on September 3rd, 1959, meaning he was about 22-23 years old when he was making
Wrath of Khan. Since I have
TWOK taking place in 2283 (15 years after "Space Seed" and the same year as the bottle of Romulan Ale), that means that David was born in 2260. Subtracting nine months from September 3rd means that David was conceived around the beginning of December 2259. Since I was already in December, I decided New Year's Eve was a logical time for Jim and Carol to get engaged.
Kirk and Carol getting together in the fall of 2257 was determined from the academic calendar of Starfleet Academy. Again, since Trek doesn't give us any real indication of what months the typical Academy year runs, I just decided to have it be the same as the real life Naval Academy in San Francisco. And since
2257 has the same calendar as 2015, you just look up
the academic calendar for the Naval Academy for 2015 and bingo, you've got Starfleet Academy's calendar for 2257-2258!
The Academy thing didn't get tricky for me until I reached
the TNG era in my timeline, as then I had to either compress or stretch when episodes took place to accommodate when in the seasons Wesley and Nog went off to Starfleet Academy or were home on school breaks. It sort of works if you squint and don't look too closely.
I do like the idea that Kirk and Carol get together, or at least get back together after the loss of the Farragut. It does make the timing a bit smoother and helps explain how Kirk might be an instructor when some other episodes suggest he is serving on a ship.
It's the first and only time they get together in my timeline. They're together from the fall of 2257 until February of 2260. I wanted them together for some time to indicate it was a serious relationship, and I needed them to break up early enough that neither one of them realized yet that Carol was pregnant. I still wanted Carol to be a decent person (If she wasn't, why would Kirk fall for her?), so she doesn't find out she's pregnant until after their breakup. Kirk is already off on another deep space assignment after more than two years of being planetside, and she decides it's best not to tell him. ("Were we together? Were we going to be? You had your world and I had mine. And I wanted him in mine, not chasing through the universe with his father.") Kirk doesn't find out he's a father until sometime in the movie era. (Either during the 2 1/2 years between TOS and TMP or the 10 years between TMP and TWOK.)
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?>
I have Kirk's past relationships in this order:
1) Ruth (~2250 - 2252 - "It's been 15 years" i.e., around the same time plebe Kirk was dealing with upperclassman Finnegan)
2) Janice Lester (~2253 - 2254 - As I said
here, I'm not sure of the exact placement of this relationship, but as I have Kirk with Carol during his entire year of Command School, this would make the most sense. As we know from "Turnabout Intruder," this relationship ended badly.)
3) Carol Marcus (Fall 2257 - Feb. 2260 - explained above)
4) Janet Wallace (2261 - Breakup in Nov. 2261 "six years, four months, and an odd number of days" before March 2268 - Janet is Kirk's first serious relationship after his breakup with Carol, which is why he remembers her so fondly)
5) Areel Shaw (2262 - Breakup in July 2262 "four years, seven months, and an odd number of days" before Feb. 2267 - another old relationship where Kirk and his ex are still on good terms)
I don't imagine that Lt. Helen Johansson is the same person as Dr. Helen Noel, if for no other reason than Helen Noel would still likely be referred to as "Doctor" instead of by her rank. I figure Helen Johansson was just a dalliance that Kirk had while he was on leave at a Starbase or something. Definitely
NOT someone under his command, as that seems to cross the line for Kirk. (Witness his awkwardness around both Janice Rand and Helen Noel - He felt weird about even
flirting with them.) And considering Kirk's embarrassment at being reminded about this past affair while in Commodore Mendez's office, perhaps Kirk resolved to have no more romantic relationships inside of Starfleet after "The Menagerie." After all, he'd have no way of knowing who might someday end up under his command.
Yes, Kirk
does seem to be flirting with the Prime Universe Marlena Moreau at the very end of "Mirror, Mirror," but since the credits start rolling before we hear anything Kirk says to her, I'm assuming he just forgot himself for a moment, quickly corrected himself, and went into professional mode once again.
I wonder how 2465 (25th century) crews will see TNG/DS9/VOY captains.
It'd serve those smug bastards right if they're just as marginalized and discounted as Kirk and his crew were by the TNG and VOY characters.
