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Confused about what happens when in Diaries of a Madman? Wonder no more with this timeline of events! Beware that spoilers are unmarked.


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     Ancient History 

Ancient Human History to the Modern Era

Events that take place from the time Discord is created, to after the fall and extinction of humanity.

  • Unspecified distant past:
    • Discord is inadvertently created by Cain.

  • Classical Antiquity:
    • Arachne is cursed with her current form by Athena.
    • Athena forms her book world and starts collecting the world's knowledge.

  • The Middle Ages:
    • Arthur and Merlin battle Discord.

  • 20XX:
    • Nav is sent back from the future for a week.
    • Humanity is nuked, resulting in the deaths of most of the species.
    • The elementals are created.
    • Nav's past self heads the team that creates the various species that would go on to populate Earth.
    • The dream machine is created.
    • Humanity goes extinct.
    • The elementals begin their mission to guide the evolution of the new races.

  • Unspecified length of time later:
    • The elementals are imprisoned.

Equestrian History

Events that took place between the downfall of the alicorns, and Nav's arrival, set several million years after the extinction of humanity.

  • Approximately 6200 years before Nav arrives in Equestria:
    • Celestia is born.
    • Alicorn civilization is destroyed by Discord.
    • Ponies are created by Discord splitting the alicorns into three.
    • Discord creates the changelings by corrupting alicorns.
    • Luna is born.
    • Celestia flees with Luna.
    • Moonbeam is corrupted into Chrysalis by Discord.
    • Celestia discovers the Elements of Harmony within Discord's lair.
    • Discord is petrified by Celestia and Luna using the Elements of Harmony.
    • Celestia and Luna gain their extended lifespans by their use of the Elements.
    • Reginald saves the ancient naga city from destruction.
    • Celestia and Luna start to stabilise Equestria.
    • The pony tribes are segregated into three to try and avoid conflict.

  • Approximately 4000 to 3000 years before Nav arrives in Equestria:
    • Luna goes on the warpath, teaming up with Reginald and anyone else who will ally with her.
    • Grogar restores the climate of the Arctic to its original frigid state, resulting in ponies being forced to migrate.
    • Celestia and Luna's efforts fail, with the lack of resources from the climate change resulting in open conflict among the tribes.
    • The Crystal Empire is founded.
    • Celestia and Luna form a system of institutional racism to bond the pony tribes together, leading to the use of terms like "anypony".
    • "True magic" is stamped out and replaced with unicorn spells by Celestia and Luna.
    • The Everfree begins appearing.
    • Grogar's experiments become dangerous and attract the attention of Sombra.
    • Sombra intervenes and puts a stop to Grogar's actions.
    • Sombra begins to be corrupted by his use of shadow crystals.

  • Approximately 1000 years before Nav arrives in Equestria:
    • The Crystal Empire disappears.
    • The Everfree becomes an issue.
    • Luna is tasked with dealing with the Everfree.
    • Luna stumbles across Discord's lair and is corrupted after looking into his magic mirror and seeing her true self.
    • Luna is banished by Celestia.
    • After Luna and Celestia's battle, the Everfree is strengthened by the ambient magic released during the fight, leading to more mutations, as well as creating the timberwolves.

  • Approximately 900 years before Nav arrives in Equestria:
    • Chrysalis asks Celestia for aid. Celestia refuses.
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     Story Timeline 

The events that take place following Discord's release, and Nav's subsequent arrival.

Year 1

  • September: (Prologue, Chapter 1)
    • Discord escapes from his confinement.
    • Nav is brought to Equestria by Discord.
  • October: (Chapters 2-4)
    • Nav meets Luna for the first time.
    • Nightmare Night festival.
  • November: (Chapters 5-6)
    • Twilight and Nav duel Trixie.
    • Nav is temporarily turned into a pegasus.
    • Twilight is briefly turned into a human.
    • Nav gains his wings permanently, following the reversal of Trixie's botched spell.
  • December: (Chapter 7)
    • Nav meets Derpy.
    • The CMC get their Cutie marks.

Year 2

  • January: (Chapter 8)
  • February: (Chapter 8)
    • Nav meets Celestia for the first time.
  • March: (Chapter 9)
    • Nav turns 19.
  • April: (Chapter 9)
    • Nav has his run-in with Pelt.
  • May: (Chapter 9)
  • August: (Chapter 10)
    • The Grand Galloping Gala takes place.
  • September: (Chapters 11-12)
    • Summer Wrap Up takes place.
    • Luna is secretly sentenced to 7 years 'house arrest' in Canterlot.
  • October: (Chapter 13)
    • Pinkie Pie's family are taken hostage by the naga.
    • Nav kills for the first time.
  • November: (Chapter 14)
    • Nav meets Lyra.
  • December: (Chapter 14, Christmas Chapter)
    • Nav brings the spirit of Christmas to Ponyville.

Year 3

  • January: (Chapter 15)
    • Nav is sent to Egypt by Celestia.
    • Celestia leaves for Israel to investigate the growing unrest.
  • February: (Chapter 15)
    • Nav arrives in Egypt with Spike, and is kidnapped by rebels.
  • March: (Chapter 16)
    • Egyptian leaders are overthrown, Nav and Spike are rescued.
    • Nav turns 20.
  • April: (Chapter 17)
    • Nav arrives in Ramla, Israel.
  • September: (Chapter 17)
    • Nav leaves Israel for Equestria.
  • October: (Chapters 18-19)
    • Nav arrives back in Equestria.
  • November: (Chapter 19)
  • December: (Chapters 20-21)
    • Fleur manages to get Rarity and Nav arrested on charges of treason.

Year 4

  • March:
    • Winter Wrap Up takes place.
    • Nav turns 21.
  • April: (Chapter 22)
    • The dragon migration takes place.
    • Luna has 5 years remaining on her sentence.
  • May: (Chapter 23)
    • Nav leaves for Egypt for the second time.
  • June: (Chapters 23-25)
    • Nav arrives back in Egypt.
    • Equestrian diplomatic mission to Egypt initiated.
    • Nav finds Taya on the streets of Catro.
    • Nav leaves Egypt for Barkelona, Spain.
  • July: (Chapter 26)
    • Nav arrives in Barkelona.
    • Nav encounters the pirates.
  • August: (Chapters 27-30)
    • Nav arrives back in Equestria.
    • Grand Galloping Gala takes place.
    • Taya badly injures Nav with a power meltdown.
    • Nav gains his extended lifespan.
  • September: (Chapter 31)

Year 5

  • March: (Chapters 32-37)
    • Maris party takes place in France.
    • Blueblood is nearly assassinated, resulting in him being poisoned and having his appearance ravaged.
    • Nav meets Cadance for the first time.
    • The changelings attack Canterlot.
    • Cadance and Shining Armor get married.
    • Nav becomes a Lunar knight.
    • The dream machine is reactivated by Nav and Luna.
    • Nav turns 22.
  • April: (Chapters 37-40)
    • Nav discovers his key, gender-switching stones, and anti-magic ring within Everfree Forest.
    • Nav meets Reginald for the first time.
    • Nav is challenged to a duel by Blueblood.
    • After losing his duel, Blueblood makes a deal with Discord.
    • Luna has 4 years remaining on her sentence.
  • May: (Chapters 40-42)
    • Gilda visits Ponyville to make amends for her previous actions.
  • June: (Chapter 42)
  • August: (Chapter 43)
    • Grand Galloping Gala takes place.
  • September: (Chapters 44-45)
    • Nav helps the changelings genocide a diamond dog clan.
    • The changelings start experimenting with human technology.
    • Ponies start experimenting with human technology.
  • October: (Chapter 46)
    • Nav accompanies Cadance and Shining Armor on a diplomatic event to the griffon capital, Gryphus, in Canada.
    • Cadance is almost assassinated by a griffon.
  • November: (Chapters 47-48)
  • December: (Chapter 49)

Year 6

  • January: (Chapters 49-50)
  • February: (Chapters 51-55)
    • Nav visits Appaloosa.
    • Nav meets Flo, and finds Excalibur.
  • March: (Chapters 56-65)
    • Fabulous Flankfurt Festival takes place in Germany.
    • Nav joins the naga.
    • Nav and Luna cause a diplomatic incident with the griffons.
    • Nav is forced into an Arranged Marriage with Gilda.
    • Nav turns 23.
  • April: (Chapters 66-71)
    • Nav and Gilda's Arranged Marriage is cancelled.
    • An assassination attempt is made on Cadance's daughter, Princess Skyla.
    • The war games exercise between the Day and Night Guard takes place.
  • May: (Chapter 71)
  • July: (Chapters 72-77)
    • Nav gets sent back in time.
  • August: (Chapters 78-80)
    • Grand Galloping Gala takes place.
    • Nav is nearly killed after declining a duel from Blueblood and being stabbed in the back.
    • Blueblood is killed by Taya.
    • Taya gains her Cutie mark.
  • September: (Chapters 81-83)
    • Nav meets Eva.
    • The griffons start experimenting with human technology.
    • Bon Bon and Lyra get married.
  • October: (Chapter 84)
    • Autumn Harvest takes place.
  • December: (Chapter 85)

Year 7

  • February: (Chapters 86-87)
    • Luna's Rambunctiously Radical Rave takes place.
    • Nav and Luna's relationship completely breaks down.
  • March: (Chapters 88-93)
    • Luna publicly confesses her crimes against Navarone.
    • Nav leaves Equestria on his quest to free the elementals.
    • Stupendous Stalliongrad Soiree takes place.
    • Nav turns 24.
  • April: (Chapters 94-100)
    • Nav arrives in the Crystal Empire.
    • Sombra is killed.
    • Aqua is freed from her prison.
    • Nav first meets Athena within her Portal Book world.
    • The Elements of Harmony are stolen by Discord.
  • May: (Chapters 101-106)
    • Nav encounters the spiders in South America.
    • The first Element of Harmony, kindness, is recovered.
    • Nav is captured by the monkeys and crowned their queen.
    • Nav's gender stones break, trapping him in female form.
  • June: (Chapters 107-109)
    • Nav arrives in Atlantis and meets the water elementals there.
    • Nav returns to Equestria and agrees to work with Miners Without Borders for his expedition to Antarctica.
    • Nav arrives in Antarctica, and discovers the human bunker.
  • July: (Chapters 109-111)
    • Nav is trapped within the bunker after the ground gives way.
    • Nav gets possessed by Ava, a ghost from the bunker.
    • Nav escapes the bunker after a week or so of being trapped.
    • Flo grows more powerful thanks to tangentially related events in the bunker.

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