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1991
Nov. 11th: Dick
Babs is 7 (Sept. 23rd, 1984). Bruce is 14 (Feb. 19th, 1977) (you know, it's when you put it like that that you really realise how close in age Bruce and Dick are).
1992
1993
July 12th: Annabeth
Aug. 18th: Percy
Dick is 1 going on 2, Babs is almost 9. Bruce is 16.
1994
Jason G., Leo, Piper, Frank
1995
1996
Aug. 16th: Jason
Percy is 3, Dick is almost 5, Babs almost 12, Bruce 19 (a baby :c)
1997
1998
1999
2000
Jan. 2nd: Tyson
Up to change
Aug. 11th: Stephanie
Dick is 8, Percy is almost 7, Jason is almost 4. Babs is closing on 16, Bruce is 23.
2001
Jan. 26th: Cass
Percy is 7, Dick 9, Jason 4. Babs is 16, Bruce is almost 24.
July 19th: Tim
Percy is 7, Dick 9, Jason 4. Babs is 16, Bruce is 24.
Thalia is turned into a pine tree at some point
Annabeth is 7, Thalia is... 14? 15? Around that.
2002
John and Mary Grayson are murdered
Sally Jackson is murdered by Smelly Gabe
Smelly Gabe is sent to prison
June/July: Dick and Percy are taken in by Bruce
Dick is 10, Percy is 8. Bruce is 25.
They are adopted some time later that same year
Sept. 8th : Duke
Dick is almost 11, Percy is 9, Jason is 5, Steph is 2, Cass and Tim are 1. Bruce is 25, Babs is almost 18.
2003
Dick becomes Robin
Babs meets Dick and Percy at a gala
She later becomes a cool older sister/young aunt to them both.
Babs becomes Batgirl
It takes her months to understand that Batman and Robin are Bruce and Dick.
2004
2005
2006
June: The Lightning Thief
Percy, Dick and Alfred are in New York when something is wrong. Grover finds them, they get separated from Alfred. On the way to CHB, Dick is "killed" (kidnapped by Hades through the Minotaur). Later, Poseidon explains the demigod world to Bruce. In late summer, Dick also learns about it.
Percy is 12 going on 13, Dick is 14
Dec 20th: Damian
Percy is 13, Dick 15, Jason 10, Steph 6, Cass and Tim 5, Duke 4. Babs is 22, Bruce is 29.
2007
Tensions start between Bruce and Dick
Teen Titans is started around the same time, end of 2006, start of 2007. Donna (Wonder Girl), Wally (Kid Flash), Kaldur (Aqualad). Dick is still Robin. Roy (Speedy) joins them in early 2009.
Golden Fleece quest
Tyson is 7, Percy 13 to 14, Dick 15
Thalia is 15
Dec. 14th to 21st: Titan's Curse
Nico and Bianca, Annabeth is captured.
Thalia is 15, days from 16 when she becomes a huntress of Artemis.
Percy chooses to be the prophecy child to spare Nico.
Percy is 14, Nico is 10 going on 11, Dick is 16
2008
Jan. 28th: Nico turns 11
Sometime before Jason is taken: Official end of Robin!Dick
Big fight between Bruce and Dick
Dick takes on Nightwing's mantel
Around February probably: Jason is taken in
Jason is 11. Dick is 16, Percy 15. Bruce is 31, Babs 23.
June: Labyrinth quest
Battle in early July, the guess is July 1st
2009
August: Battle of Manhattan
The world thinks it was a Wonder Woman mission. She did participate alongside the gods in the fight against Typhon.
Zeus, in his amazing stupidity, decides that it was A Bad Move. His justification is that she is a well known figure to mortals and, thus, her participation "attracted their attention and endangered the Ancient Greek world" or whatever. He banishes her for 5 years in punishment. She spends those 5 years in space.
Aug. 18th: The Second Titan War is over
Percy is 16. Jason is 13.
Early December: Jason is killed by the Joker
After discovering Catherine isn't his birth mother, Jason decides to find the latter. Bruce supports his efforts. However, once he finds Sheila, Jason wants to go to her immediately, while Bruce argues that he should wait for Bruce to do an additional background check on her. Percy agrees with Bruce. Jason runs away (still in Gotham), right into a trap. Joker kills him. Bruce is too late.
Dick is out in space for a mission with the Teen Titans. Jason was 13.
Dec. 14th: Percy goes missing
Jason's funerals were just a few days before
Dick is 18, Percy is 16, Jason was 13. Steph is 9, Cass 8 on 9, Tim 8, Duke 7. Damian is almost 3. Bruce is 32, Babs is 25.
Second half of December: quest to save Hera (Jason G., Piper and Leo)
2010
Early months: Joker attacks Babs, leaving her paraplegic
April: end of Percy's nap
Starts his training with Lupa
April/May: Jason wakes up in his grave
He wanders around, a few inches from brain-dead. He's found far from Gotham and gets taken to a hospital as a John Doe. Coma.
Mid-June: quest to rescue Thanatos
Percy is 16, Frank 15, Hazel 14
Rest of June: Start of the Prophecy of Seven
July 1st: Annabeth and Percy fall into Tartarus
July 18th: Annabeth and Percy come back
Yup, Annabeth spent her 17th birthday in Tartarus, lucky her
Aug. 1st: End of the Second Giant War
Percy and Annabeth are 17
Percy doesn't go back to Gotham.
2011
January: Jason wakes up from his coma
Amnesiac, and unnamed since he hasn't turned up as a missing person (because, ya know. Dead person instead). Talia somehow does learn of him and gets him from the hospital. She brings him to the League of Assassins, pushes him into the Pit to restore his health and memories.
Jason is 14. Damian is 4.
March 31st: Jason G. dies
He was 16.
2012
2013
Tim becomes Robin
Tim is 12/13.
Depending on when Tim takes the mantel, Bruce would have had no Robin for 3 to 4 years, which made him spiral hard.
Percy is 19 (away), Dick is 21 (and angry away, but will make an effort for Tim), Jason is 16 (away with the league). Bruce is 36. Babs is 28/29.
2014
Blockbuster, Tarantula
2015
February: Tim abandons Robin, Steph takes it up
Tim is 13
30th March: Steph is kidnapped, tortured, and then "killed" by Black Mask
Steph is 14. Leslie saves her but decides to fake her death to teach Bruce a lesson. With Steph's mom and grandma's approval, Leslie takes Steph with her on a months long humanitarian mission, during which Steph does her reeducation. She gains back almost all of her mental and physical abilities.
In the mean time, Tim becomes Robin again to avoid another spiral from Bruce.
Tim finds Cass and brings her to Gotham
Cass is 14. Bruce is 38.
The Batarang Incident
July/August: Steph comes back "to life" as Spoiler
Steph is 15.
Dick 23, Percy 21/22, Jason 18/19, Tim 14.
2016
Mid-2016: Damian arrives in Gotham, Bruce "dies"
Damian is 9. Bruce is 39.
In a matter of weeks after Bruce dies, Jason leaves and ends up forming the Outlaws with Roy and Kori, Cass leaves for Hong-Kong, and Tim leaves to find Bruce.
2017
Early: Duke's parents are jokerized
Duke is sent to foster care. Only weeks later he joins the We Are Robin movement. He is 14.
June-ish: Bruce comes back
Which solves some issues but creates a bunch of others.
August-ish: Duke becomes Bruce's ward
Duke is almost 15, he starts training to become Signal.
Steptember: Damian dies
He is killed by his adult clone. Damian was 10.
Damian's death is not announced to the public.
Late november, early december: Dick dies/"dies"
Dick as Nightwing is attached to a bomb linked to his heartbeat; the only way to stop it is to stop his heart. Lex Luthor forces a pill down his throat to stop his heart. Contrary to canon, in this version, Lex does not give Bruce the reversal pill, he just runs away as soon as he can while Bruce unplugs Dick from the machine and starts CPR.
Dick is revived but stays in a coma for some time as his body recuperate. When he wakes up, he learns that his funerals have already passed and that Bruce wants to send him to Spyral without letting him say the truth to his siblings. They fight. Dick loses and is made to leave.
Dick's death is announced to the public. For Percy, that's the sign that he will never come back to Gotham.
Dick is 26, Percy is 24, Jason is 21, Steph is 17, Cass and Tim are 16, Duke is 15. Bruce is 40, Babs is 33.
December: Damian's revival
After much happening, Bruce is made to choose between reviving his parents or Damian and chooses Damian. This happens days after Dick leaves for Spyral.
Damian is 11.
2018
Duke becomes The Signal
Duke is 15.
June/July: Bruce's amnesia
Even once he regains his memories, he still doesn't remember anything from Dick's death to the day of the spell.
In the absence of news from Bruce, Dick decides to wrap up the mission as fast as possible to come back to Gotham and check for himself.
October: Dick "comes back to life"
Early november: Dick being alive and not dead is announced publicly
(Also early november, Kimmie turns 5)
November 9th: Percy arrives in Gotham
This is the start of OBBAF ✨
Dick is 27 (in two days), Percy is 25, Jason is 22, Steph is 18, Cass and Tim are 17, Duke is 16, Damian is 11 (closing on 12). Bruce is 41, Babs is 34.