Just wondering if I can get a timeline for the Freeport Stories. I just finished reading the first two, but after that it seems a bit vague exactly which ones are sequential. Mainly cause a few of them are listed directly as a squeal to the Freeport Venture base story so it's a bit confusing what would be next chronologically.

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While the exact amount of time that elapsed is vague, as far as chronology goes, the stories are insofar also published chronologically (as in you can check when it was posted).

But to save everyone the effort:
In order
Moment in the Sun
Freeport Venture
More Equal than Others
Auction Night
The Hunted
Something Sweet and Sour
A Thousand Masks

Seems odd that Starlight Glimmer stuff happens that early. It was always my impression that Sunset Shimmer had her falling out with Celestia around a decade prior to the start of the show. Since it is suggested that it happens before Twilight gets her cutie mark and therefore becomes Celestia's new student. You gotta figure growing up, finishing the school as it does look like Twilight isn't taking classes anymore when she figures out about Luna's return as Nightmare Moon.

Then a few more years before they go and stop Starlight and her village. Though I guess it might take place before all that, will need to read it to check.

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Starlight was shown to be younger than Sunset, and very naive... kind of a straw political type who bristles when her own rules are applied to her. She had to start somewhere before moving to Our Town, and apparently that somewhere was Freeport in the Winningverse.

Just finished reading that one. It seems that the Winningverse Starlight is different than the Showcanon. Spoiled brat verse fillyhood issues about being abandoned by friends.

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Yeah, that Starlight was written with only the Season 5 Opener as reference. It was assumed at the time her beef was with inequality, not cutie marks.

So naturally, in the event that Starlight makes an appearance again in Winningverse, I do not expect her to match up with canon Starlight at all.
Time will tell, I suppose.

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Starlight's next appearance in the Venture series is going to be building off her appearance and backstory in "More Equal Than Others." Partly because that's already established, and partly because I'm not wild about what the show's done with her since the Season 5 opener.

It's as Swiftest says. More or less, the stories chronology will be based on when they are posted, at least to this point.

As for Starlight, the story she featured in was written before the season finale she was in had aired, and these stories have the AU tag for a reason. Also some of us weren't completely pleased with Starlight's...reasonings for why she did what she did.

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Only makes sense that in an AU about the superior horse, Starlight gets improved by proxy.

So a thought struck me and I wanted to check it out.

Mother's Day happens.
+ 3 months. Meeting Candence and running away.
+ ? months (Implied to be small so lets say 1)
+ 1 month. Traveling to Freeport and dealing with Mome.
+ 3 months. Building her tower.
+ 2 months. Everything after that, since the stories metion the one just prior to it as the last major case and doesn't seem to state more than a week or two passing between.
= about 10 months roughly.

Mother's Day will be taking place soon again in the Freeport series, also just when is Sunset's birthday? Cause I think Celestia would at least send something to her as a gift.