After much thought, and careful consideration, I have finally created a timeline that contains almost everything that occurs in my stories. In this post, you can see exactly what happens to which ponies, and how they all cross over, as many of you have pointed out in the fics themselves! This blog post with also be updated as time goes on.
Here's the full day-by-day graph of all the events so far. Each "darkened" block symbolises a time-skip, where the fic goes by without you actively reading it (most of those days are explained in the fics themselves, however). And the two blurry additions on the bottom? Certainly not me planning anything major... no siree.
Anyway, here we go with the list of what happens each day. Spoilers below, of course. Quick warning; it's gonna be a long list!
The events of The Pact occur shortly after Nightmare Moon’s defeat in Season 1. Therefore, the fic does not appear on this timeline.
Spreading Your Wings and Hers occurs in its entirety.
Love Life Starts. The Broken Hearted stallion tries to jump off Town Hall while drunk, Pinkie saves him.
Pinkie Pie agrees to help the Broken Hearted over his depression.
The Poison of Passion starts. The Slacker and Zecora meet for the first time.
(Crossover Point. Pinkie sees the Slacker hopping from cloud to cloud, looking for Zecora.)
Even Kindness needs Kindness starts. Fluttershy meets the Passer-By, both get trapped in a mud-cave etc.
Zecora and the Slacker humiliate a racist merchant in Ponyville Market, gain a month’s supply of chilli pepper powder.
To be Young and Stupid starts. Apple Bloom and the Youth first become friends.
More Than Buddies occurs in its entirety.
(Crossover Point: Dinky Doo’s “chocolate muffins” moment.)
The Passer-By wakes up the next day on Fluttershy’s sofa. They agree to a date. Even Kindness Needs Kindness ends.
(Crossover Point: The Passer-By and the Buddy are revealed to be roommates.)
A storm appears over the Everfree, quickly dispersed by the Slacker and the weather team.
The Youth and the Cutie Mark Crusaders hang out, draw out Cutie Mark-gaining plans.
The Cutie Mark Crusaders try for a “Teacher Bodyguards” Cutie Mark. They fail.
Her Whole Darn Heart starts. Applejack and the Human watch the sun set.
What Happens in Pegasus starts. The Rookie and Rainbow Dash get in a fight, break up.
Reconciling Annabelle Smith starts. The retired Scarlet Wing reminisces, interrupted by an old friend.
(Crossover Point. The Rookie and the Scarlet Wing meet up)
The Youth sketches Apple Bloom’s face while daydreaming, gets embarrassed.
The Human’s Welcoming party occurs. Involves hoof-wrestles, kisses, vomiting, runaways and narrowly-avoided permanent transformations. Applejack and the Human make love.
The Scarlet Wing helps the Rookie, sends him back to Ponyville.
The Human wakes up the next morning, resolves to live in Equestria for the rest of his life. Her Whole Darn Heart ends.
The Rookie and Rainbow Dash make peace with each other.
(Crossover Point: The Human watches RD and the Rookie reconcile from a distance)
The Youth and the Cutie Mark Crusaders nearly burn their tree house down.
Rainbow Dash and the Rookie visit Las Pegasus, crazy things happen…
The Scarlet Wing sees Granny Smith for the first time in sixty years. They spend the whole day catching up.
The Scarlet Wing and Granny Smith visit the park, play chess, have a meal etc.
(Cameo Point: Ditzy, Dinky and the Buddy are the “frisbee-playing family”.
Reconciling Annabelle Smith ends.
Desire and Deep Water starts. Twilight Sparkle freezes Ponyville Lake, falls though ice, nearly drowns, loses ability to use magic via minor hypothermia.
The Lake Warden offers to aid in Twilight’s recovery. They tell him to return tomorrow evening.
The Lake Warden starts helping Spike and Twilight.
The Youth and the CMC finish rebuilding the tree house. Apple Bloom pecks the Youth on the cheek. To be Young and Stupid ends.
Zecora tells the Slacker about the Silver Tulip. They agree to find it together tomorrow.
Zecora and the Slacker look for the Silver Tulip. Attacked by a cockatrice, and later a four-headed cobra. The Slacker confesses love to Zecora, they reconcile and sleep in the same bed.
The Lake Warden and Twilight talk about themselves for a while. Spike finds out about Twilight‘s crush on him.
The Lake Warden sees Twilight panic over her lack of magic. They reconcile and agree to visit friends more often.
Day 24 - Day 27
The Lake Warden and Twilight visit various friends and hang out together.
Twilight and the Lake Warden receive free milkshakes from Sugar Cube Corner. They kiss for the first time.
Pinkie Pie discovers that she has strong feelings for her friend, the “Broken Hearted” stallion.
(Crossover Point: the “Milkshake” scene from two angles.)
Fleur-de-Lis returns to mock the “Broken Hearted”. Pinkie shoots her out of a Party cannon. Love Life ends.
Fabulosity in Fact starts. The Celebrity discovers a news story that destroys his reputation, and decides to flee to Ponyville in shame.
(Crossover Point: Fleur’s controversial method of transport)
Twilight finally thaws the lake, she and the Lake Warden spend the whole day there playing and eventually make love below (and later above) the lake’s surface.
The Celebrity meets Rarity for the first time, arranges to meet in Spa. Rarity agrees to help the Celebrity and offer for him to stay the night for (actual) coffee.
A Lover’s Choice occurs in its entirety.
(Crossover Point: Fabulosity in Fact and A Lover’s Choice briefly cross paths in the spa)
Twilight and the Lake Warden wake up on the lakeside the next morning. Desire and Deep Water ends.
The Celebrity and Rarity return to Canterlot via train. They settle at Canterlot Palace.
Day 31 - Day 32
The Celebrity helps Rarity with her clothing line.
The Celebrity and Rarity nearly make love, but decide to hold it off until the dresses are finished. While buying more fabric and gems, Rarity foils an attempted mugging and gains two thousand bits bounty. Rarity and the Celebrity make love shortly after.
Love-locked and Breathless starts. The Scoundrel attempts to mug a rich pony. Is knocked unconscious by an unknown vigilante and arrested.
(Crossover Point: the whole “Mugging” scene.)
Rarity leaves Canterlot that night, after working alongside the Celebrity and his magazine.
Rarity arrives in Ponyville the next morning. That night, the Celebrity meets Octavia for the first time. Fabulosity in Fact ends.
Zecora and the Slacker make love. The Poison of Passion ends.
The Scoundrel is granted bail on the condition that he works for Trixie. An agreement is made.
The Scoundrel tries to teach Trixie the secret of opening locks via magic. Trixie fails, but starts practicing the trick in secret.
The Scoundrel’s debut as Trixie’s assistant. He misbehaves on stage, shows off his talents and becomes an instant hit.
The Scoundrel takes Trixie to a pub, where they finally open up to each other and swap origin stories. A good night out getting drunk.
The Scoundrel and Trixie get in an argument, the Scoundrel storms off. Trixie attempts an underwater-escape cell stunt, nearly drowns. Scoundrel returns and saves her. The Scoundrel and Trixie make love. Love-locked and Breathless ends.