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#I'm going to reblog the last 10 pages onto this post as soon as it comes off the queue
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Timeline: Batman
google doc / ao3
This is my best attempt at a post-crisis timeline based on age-- specifically Bruce’s age every time he adopted and/or met one of his children. 
List of events:
Bruce’s parents die
Bruce becomes Batman
Dick’s parents die
Dick becomes Robin
Jason becomes Robin and is adopted
Jason dies
Tim becomes Robin
Cass appears
Dick is adopted
Tim is adopted
Cass is adopted
Damian becomes Robin
I’ll be citing my work by issue and panel. This isn’t my most organized work, and I don’t know how well tumblr will let me translate it, so I do recommend the google doc. I imagine the image quality here won’t be great. 
Notes:
This is a post-crisis timeline (1986-2011). I’ll be referencing a few pre-crisis panels, but I won’t be touching the New 52 or anything after it. That’s a different game of ball with its own, extremely bad, timeline.
Crisis on Infinite Earths is a 1985-1986 series that rebooted the DC timeline and altered some backstories, including Jason’s. Pre-crisis, his backstory was almost identical to Dick’s. Post-crisis, he changed to the “steal the wheels off the Batmobile” origin. Anything written before 1986 is a weak source for my purposes. 
My original question centered around Bruce’s age through the process of meeting and acquiring his children. In this timeline, those children are (1) Dick Grayson, (2) Jason Todd, (3) Cassandra Cain, (4) Tim Drake, and (5) Damian Wayne. I was envisioning an interview where the kids explain their family timeline to outsiders. I did not anticipate the project taking this long. 
We’re talking about 72 years of content here, which means decades of contradiction, conflation, and rewrites. I’m pretty satisfied with my work product, but please understand that there are no perfect answers. I’m going to cite my sources, and I’ll do my best to explain why I chose those sources specifically, but it’s pretty likely that for every panel I pull, there will be others with different numbers. We’re all going to have to live with that. 
Event timeline
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*I’m defining Jason’s age by the time elapsed since his birth, but you could make an argument for using time he has been alive, which is, of course, different. That’s why the parentheses are there. 
Age differences
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As Robin
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Bruce’s parents die
Pretty consistently, Bruce is written as eight years old the night his parents died. 
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Detective Comics #0 (1994)
This is a zero issue where Bruce thinks back on his origin story. It was written long after Crisis on Infinite Earths (1986), and I tend to give a lot of weight to ages written in summaries of past plot lines, my reasoning being that it’s easier to be consistent in one issue than it is to be consistent through a month to month story. 
Bruce first appeared as an adult in Detective Comics #27 (1939), and the Waynes were already dead at that point, so flashbacks are the only available material anyway. 
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Gotham Knights #6 (2000)
The text is Hugo Strange talking about Bruce, and the image is Tim and Dick playing at Wayne Enterprises. 
I’ll take a second here to note that I did find at least one alternate age for Bruce— in Superman/Batman Secret Files & Origins (2003), Bruce was 10 when his parents died. I’m disregarding that in favor of the stronger 8 year old timeline, especially in light of Batman #404 (1987).
Batman #404 is the beginning of Batman: Year One, which was explicitly written to clarify the Batman timeline post-crisis, and it’s the basis of most of my calculations for Bruce and Dick’s ages.
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Bruce becomes Batman
According to Year One, Bruce was 26 years old when he became Batman. I’m using his age at his parents’ deaths, his age when he returned to Gotham, and his 18 year timeline.
Batman #404 puts Bruce at age 25 when he returned to Gotham in January. 
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Batman #404 (1987)
Bruce gives his dramatic, “Yes, Father, I will become a bat,” line in March. In the same scene, he says that it has been 18 years since his parents’ deaths. Knowing that they died when Bruce was eight, that puts Bruce at 26 years old the day he became Batman, which makes sense considering Bruce’s birthday is usually set at February 19th. 
He was 25 in January, turned 26 in February, and became Batman at 26, 18 years after his parents’ death. 
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Batman #404 (1987)
Post-crisis, DC built timelines off the “Year” model. Year One is Batman’s beginning, and events after that are measured by how far away they are from the year Bruce became Batman. I’ll be using the Year model for Dick’s life events next. 
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Dick’s parents die
The Graysons died in Year Two. Using the Year Model, Dick was 12 when his parents died, and Bruce was 37. 
Year timelines appear a fair amount, especially in issues titled “Secret Files & Origins.” I pulled this bit from Batman Secret Files & Origins (1997) because it was the easiest to screenshot. 
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Batman Secret Files & Origins (1997)
Year Two would place Bruce at 27 years old. I’m calculating Dick’s age backwards, based on him being 13 years old during Year Three. 
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Batman Secret Files & Origins (1997) 
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Dick becomes Robin
Dick became Robin in Year Three, when he was 13 years old and Bruce was 28. I’m using two different issues to calculate the number. 
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Batman #441 (1989)
Batman #441 is from Tim’s introduction story. It takes place “months” after Jason’s death. We’ll get to that part. In Batman #441, Tim asked Dick to be Robin again in order to help Bruce, who was visibly unstable after Jason’s death. Dick says that he can’t go back to being Robin, just like he can’t go back to being 13 years old. The strong implication there is that Dick became Robin at 13, which corresponds to Dick’s statements in Batman #416 (1988). 
In Batman #416, Dick as Nightwing returns to confront Bruce about Jason becoming Robin. He says that he was Robin for six years, and he stopped being Robin at 19.
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Batman #416 (1988)
If Dick stopped being Robin at 19, after 6 years, that would put him at 13 when he debuted as Robin, the same number from Batman #441 (1989).
Dick was 13 during Year Three, so 12 during Year Two, the year his parents died. Those numbers answer the first bit of my original question. I wanted to know how old Dick and Bruce were when Dick became his child. It’s a bit more of a complicated question for Dick, since he was originally Bruce’s ward, then adopted as an adult. 
Based on the timeline so far, Dick became Bruce’s ward at 12 years old, while Bruce was 27.  
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Jason becomes Robin and is adopted
As previously discussed (see Notes), Jason’s timeline is complicated by Crisis on Infinite Earths (1985-1986). Pre-crisis, Jason first appeared in Batman #336 (1983) as a former circus acrobat very similar to Dick.
Jason’s origin story reboots at Batman #408 (1987), which describes the switch-off between Dick and Jason. I’m building a lot of my timeline off of that issue. At the beginning, Dick gets shot by the Joker, and as Bruce carries him away, the media ask if Robin is dead. Dick isn’t dead, but back at the manor, Bruce decides to retire Robin as a role, based on the idea that crimefighting is too dangerous for a child. 
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Batman #408 (1987)
This version is more or less from Bruce’s point of view, but there’s a contrasting version from Dick’s point of view later, in Batman #416 (1987). That one has a significantly different tone, and I already cited it once (page 13) because Dick talks about his age and the amount of time he was Robin.  
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Batman #408 (1987)
The second part of the issue takes place “weeks” later. Bruce goes to Crime Alley to mourn his parents on the anniversary of their death. He comes back to find that somebody stole the wheels off the Batmobile. The somebody was Jason, and by the end of Batman #409 (1987), Bruce is calling Jason “Robin.”
Batman #408 (1987) seems to divide Dick’s departure and Jason’s introduction by only “weeks,” in the post-crisis reboot. Dick’s version of the story in Batman #416 (1987) is much less charitable to Bruce— instead of ending on a panel of Bruce smiling, it shows the aftermath of Dick in tears as Bruce walks away. Dick goes on to describe leaving the house, going to college for a semester, then dropping out. According to Dick, Bruce didn’t even say goodbye. 
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Batman #416 (1987)
I don’t think the stories are contradictory; they’re just different experiences of the same events, separated by only eight issues. Dick tells us that he was 19 when he left Wayne Manor, and Bruce chooses his new Robin “weeks” later. 
As a summary, we know that Bruce’s parents died when he was eight, and that 18 years passed before he became Batman at 26. One year later, Dick’s parents died while Bruce was 27. One year after that, Dick became Robin at the age of 13. From those facts, Bruce is 15 years older than Dick. 
All of my calculations of Bruce’s age are based off of the age gap between him and Dick. Dick was 19 when Jason became Robin, so we know that at that time, Bruce was 34. We also know that at that time, Jason was 12. 
I can’t show a source for that number because it appears on the letter page of Batman #408 (1987), Jason’s introduction.
Even after a significant amount of investigation, I can’t find a copy of the letter page, but it’s cited by enough secondary sources for me to be comfortable using it. That issue is specifically written to show Jason’s origin, so it makes sense that it would contain Jason’s age at inception, even if the number wasn’t in the actual exposition. 
From Jason being 12, we can establish a seven-year age gap between Jason and Dick, who was 19 at the time. Now we know Bruce, Dick, and Jason’s ages, and the age differences between them.
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Back to my original question— when did Bruce acquire Jason? We know that Bruce was 34 when Jason became his ward, and Jason was 12. The next question, however, is when did Bruce adopt Jason? On this one, I’m making an educated guess. 
Again we have to differentiate between pre-crisis and post-crisis timelines. Pre-crisis, there’s a full storyline about the fact that Bruce did not adopt Jason, although not for lack of trying. In Batman #374 (1984), the Child Welfare Bureau investigates Bruce when it notices that Bruce has not adopted Jason— and is not even, in fact, his legal guardian. 
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Batman #374 (1984)
The rest of the storyline is about Jason’s custody. A villain named Natalia Knight (Nocturna) adopts Jason in an attempt to get Bruce to marry her in order to become Jason’s father. In the court scene in Batman #377 (1984), Bruce says that he filed to adopt Jason sometime beforehand, although it’s unclear to me whether he means he filed between those issues or the CWB documents were incomplete.
Natalia does adopt Jason in Batman #378 (1984), and he briefly lives with her before returning to Wayne Manor in Batman #381 (1985), directly before the reboot. 
I’m including all of that for two reasons: first, I do think it’s important to clarify both this version and the post-crisis version I’m about to address. Second, I spent years under the impression that Bruce adopted Jason pre-crisis because of one, well-known scene. 
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Batman #377 (1984)
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Batman #378 (1984)
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Batman #381 (1985)
Donna Troy gets married in Tales of the Teen Titans #50 (1985). At the wedding, Bruce and Dick have a conversation about Jason and about their own relationship. A few of those panels get spread around because they contain what I would consider a defining moment between Dick and Bruce. 
I’m certainly not complaining about the amount of times I’ve seen the wedding conversation, but I think that, in regards to Jason, seeing just those panels has created a misconception.
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Tales of the Teen Titans #50 (1985)
Without context, it looks, at least to me, like Dick is saying that Bruce has adopted Jason pre-crisis, which isn’t true. This issue takes place between the Natalia adoption in Batman #378 (1984) and Jason’s return to the manor in Batman #381 (1985), and the panels directly before the exchange make that clear. I just didn’t see those panels until I looked through the whole issue for this project. 
I’m reasonably certain that in the past, I publicly cited this issue as evidence of Jason’s adoption, and I was wrong about that. [Note: As it turns out, I was only partially wrong. See section Correction.]
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Tales of the Teen Titans #50 (1985)
As we see, the wedding conversation is in the context of the Natalia adoption. With that cleared up, and with the pre-crisis timeline filled out, let’s move to post-crisis. 
In my brief read-through of Batman #404-427 (1987-1988), I didn’t find any direct references to Jason’s status. Those issues begin at the reboot and end at Jason’s death. However, Dick and Jason’s statements after the fact do tell us that post-crisis, Bruce did adopt Jason. 
In Batman #436 (1989), Dick returns to the manor in the direct aftermath of Jason’s death, and while he is there, he sees that Bruce removed any trace of Jason from the house. There aren’t any trophies in the Batcave, and there aren’t any pictures of Jason on the nightstand displaying Bruce’s family photos. 
Dick says that Jason was Bruce’s son.
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Batman #436 (1989)
I think it’s fair to ask whether Dick is being literal here, because even if Bruce hadn’t legally adopted Jason, it would still be more than appropriate to call them father and son. I’m not going to place my opinion solely on this kind of statement, even if it does appear pretty regularly from 1988 to the end of the timeline.
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Green Arrow/Black Canary #4 (2007)
We get a more definite answer later, during Tim’s first appearance. In Tim’s origin story, he deduces Batman and Robin’s secret identities after he sees footage of Robin doing a type of flip that only the Flying Graysons could do. Tim was at the circus the night Dick’s parents died, so he saw Dick do the flip there, then saw Dick become an orphan. 
Because Tim knew that Dick was the first Robin, he correctly identified Bruce as Batman and Jason as the second Robin. He tells Dick all of this in Batman #441 (1989).
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Batman #441 (1989)
Tim does specifically use the word “adopts” here, and that’s good enough for me. The last part is guesswork— I don’t know for certain how old Jason and Bruce were when the adoption took place, but I’m electing to say Jason was 12, the same age as he was when he became Robin. 
I picked that number both out of convenience and because Tim seems to be putting Jason’s adoption and the second Robin’s appearance at around the same time. With that in mind, I think that Jason was 12 years old both when he became Robin and when Bruce adopted him. Using the age gap we already established, that would put Bruce at age 34. 
Circling back to my original question, Dick became Bruce’s ward when Dick was 12 and Bruce was 27. Jason became Bruce’s ward, then adoptive son when Jason was 12 and Bruce was 34. 
At this point in the timeline, Bruce is 34 with one former ward and one adopted son. 
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Correction 
A few days after I wrote my section about Jason’s appearance and adoption, I realized that I was missing a panel citation in my discussion of Jason’s death. The panel is from New Titan #55 (1989), and you’ll see me cite it when I talk about Jason’s death certificate. 
New Titans #55 (1989) is the issue where Dick, who is with the Teen Titans,  finds out about Jason’s death. While I was combing through the issue for the panels I wanted, I reread a scene I had completely forgotten about. Dick goes back to the manor to speak to Bruce, and it doesn’t go well.
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New Titans #55 (1989)
I have three comments here. First, I do think this scene is inconsistent with the simultaneous story in the Batman title. In this version, Dick and Bruce have a very aggressive confrontation, but in Batman #436 (1989), Dick appears to be returning to the manor for the first time since Jason died, and there isn’t any reference to a prior fight. 
Putting that aside, Bruce does explicitly say that he adopted Jason, and that’s more, stronger verification of a post-crisis adoption. Lastly, it’s pretty clear that Bruce and Dick are talking about the wedding scene. 
I already explained that the wedding scene is pre-crisis, and in the original text, that conversation is about Bruce wanting to, but not being able to, adopt Jason. New Titans #55 (1989) carries the wedding scene into post-crisis canon, changing the language in the process. In this version, Bruce has adopted Jason. 
I was still wrong about the wedding scene because in the past, I used it as evidence of a pre-crisis adoption. It isn’t pre-crisis evidence, but it is, in a roundabout way, evidence of the post-crisis adoption. I wanted to clear that up before I move on to Jason’s death. 
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Jason dies
Jason’s death is by far the shakiest point on my timeline, but I’ve chosen to put him at 15 the day he died in Batman #427 (1988). 
I think it’s safe to say that Jason was either 14 or 15 when he died, and my basic conclusion is that running numbers doesn’t give me a definite answer. There’s a cop-out option based on an extraordinarily poor source, and I’m taking the cop-out. 
The general consensus seems to be that Jason was 15 at his death, citation to Jason’s death certificate. Jason’s death certificate appears in two different places, and I think most folks conflate the two. 
To my knowledge, the only copy of Jason’s death certificate in full appears in The Batman Files (2011), where it does list Jason’s age as 15. 
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The Batman Files (2011)
Now there is a partial copy in Batman Annual #25 (2006), which I would argue is a very reliable reference when it comes to Jason. That issue is part of the Under the Red Hood story, the one where Jason returns to Gotham for the first time after his resurrection. In fact, the specific annual issue has a timeline for Jason’s events counting forward from his death. 
Here’s the problem: the issue doesn’t say his age at death. The partial copy of his death certificate looks like this. 
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Batman Annual #25 (2006) 
I think that when most folks remember a death certificate, they think of this one, the one from a very important issue, instead of The Batman Files (2011) which, as noted, is a very bad source. 
I have three issues with The Batman Files (2011): the format, the publishing date, and the other information on the certificate. First, The Batman Files (2011) isn’t a comic book at all. It’s a commemorative book published in collaboration with DC in 2011. Now I don’t think that fact completely removes the book as a source, but it certainly damages its value as one. 
My problem with that date, 2011, is that it’s the year the New 52 premiered. I called it a commemorative book because it’s meant to be a look back at a fully complete timeline, a kind of “this is us saying goodbye” product. The date and format alone make me hesitant to cite the certificate, but on top of that, the certificate is inconsistent with prior canon. 
I am intimately familiar with retcons and conflicting numbers in the DC timeline. I made a point at the beginning of this paper to tell you that although this is my best attempt to make a cohesive timeline, assuming that I can carve out a cohesive timeline is fundamentally flawed. 
I’m not saying that a single contradictory number is enough to make me disregard a source. I am saying that in this particular conversation about an already suspect source, I’m going to take inconsistency into account. 
In New Titans #55 (1989), the issue from Corrections, Dick finds out about Jason’s death because a team member notices Jason’s status is set at “unknown.” Dick uses Bruce’s passcode to access restricted information, and he and the Titans see that Jason’s real status is “deceased.” 
The death certificate in The Batman Files (2011) marks Jason’s height at 4’6 and his age at 15. In contrast, Dick’s scene puts Jason at 5’4, and its only reference to Jason’s age is a very relatable question from Donna. “How old was he, anyway?”
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New Titans #55 (1989)
There’s a substantial difference between the two heights, and I think it’s also worth noting that for a 15 year old American male, 4’6 is in the 0.1 height percentile. In the past, I and many others have tried to justify that height along the lines of Jason being malnourished or similarly afflicted. Personally, I liked the parallel between this height for Jason and Damian’s height at his own death in 2013, and I know I’ve talked about that in the past.
I’m not criticizing anyone for using the 4’6 number, but I do think the unlikelihood of a 15 year old that size is worth bringing up. 
In summary, The Batman Files (2011) is so bad of a source that I’m only willing to use it as a last resort. Unfortunately, it’s time for a last resort. 
I mentioned a timeline in Batman Annual #25 (2006) that counts forward from Jason’s death. I’m not going to use image cites here because they’re just isolated text boxes labeled either “six months later” or “one year later.”
Using that timeline, we know that Jason’s resurrection took place six months after his death. He spent one year in a coma, then one year on the street, then one year with the League of Assassins. Finally, he spent a nebulous time training before he returned to Gotham. 
We know that Jason was gone for a minimum of three and a half years, then whatever time “training” includes. Personally, I’m applying my best attempt at comic logic to say he was missing for somewhere between three and four years. 
To understand the next bit, I need to point out that from Jason’s death on, I’m going to be using Tim’s age to track time in the same way I’ve been using Dick’s so far. 
As a reminder, I know what age Bruce was when Dick became Robin (28), and I know Dick’s age at the same point (13), so I know there’s a 15 year age difference. As I track Dick’s age through the timeline, I add 15 to get Bruce’s. 
In the same way, I know what age Dick was when Jason became Robin (19), and I know Jason’s age at the same point (12), so I know there’s a 7 year age difference. I can use that number ongoing. 
I know that Tim was 13 when he made his first appearance as Robin, and I’ll get into that in the next section. After that, I’m placing Dick, Tim, and Cass’s adoptions based on Tim’s age. 
To do that, I need to know how much older Dick is than Tim, and I can only get that by knowing Jason’s age at his death, sort of. 
How long was Jason Robin? If I had that information, I could establish Jason’s age by counting up from 12, the age when he became Robin, then establish Tim’s age from there.  
I can’t really answer that question. There is a panel from Batman #436 where Dick, apparently in his first time at the manor since Jason’s death says the following. 
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Batman #436 (1989)
My instinctual interpretation is it’s been two years since he stopped being Robin at 19, making Dick 21 and Jason 14. In my opinion, that’s straightforward plain language, but it seems like I’m in the minority on that one, and most folks read it as Dick saying it’s been two years since he was last at the manor. We know from Batman #416 (1988) that Dick’s last visit to the manor was 18 months after Dick left home. 
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Batman #136 (1988)
I think the most honest thing to say is that Jason was Robin for an indeterminate amount of time that was somewhere between two and three years. I don’t know which number is closer. I also, if you remember, think that Jason was gone from Gotham for somewhere between three and four years, but I don’t know where in that range the real number is. 
Here’s why absolutely nothing I’ve said in the past seven pages matters: I need to build my timeline based on the age gap between Jason and Tim. 
I don’t know how old Tim was when Jason died. 
I know how old Tim was at his first appearance as Robin, and that’s a different number. 
We’ll finish this conversation in a moment.
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Tim becomes Robin
We begin, thankfully, with a straightforward fact. Tim’s first storyline spans Batman #440-442 (1989). The arc is called A Lonely Place of Dying, and we already talked about it. Tim, having watched Batman and Robin from the shadows for years, comes forwards in the aftermath of Jason’s death in an attempt to convince Dick to become Robin for a second time.
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Batman #441 (1989)
We know that Tim was 13 years old at the time, but I do need to clarify exactly what time that was— an indeterminate amount of time after Jason’s death. 
The word that pops up a couple of time in Tim’s first arc is “months,” from Tim and Two-Face. How many months? Who’s to say. 
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Batman #442 (1989)
So, from the top. We know that Bruce was eight when his parents died, 26 when he became Batman, 27 when he met Dick, 28 when Dick became Robin, and 34 when he met Jason.
Dick was 12 when he met Bruce, 13 when he became Robin, 19 when he left home and Jason became Robin. 
Jason was 12 when he became Robin.
Bruce is 15 years older than Dick. Bruce is 22 years older than Jason. 
Dick is 7 years older than Jason.
How long was Jason Robin? Unknown, but somewhere between two and three years. At that point, he died. “Months” after that, Tim was 13. 
Here, we need to acknowledge that Jason could have been either 14 or 15 at his death, and at the same time, Tim was either 12 or 13. We need to know how far they are apart to calculate Tim’s age in relation to Jason, Dick, and Bruce— ongoing, we will always know exactly how old Tim is, so (if we know how far apart Jason and Tim are) we will always know Bruce, Dick, and Jason’s age from there. 
How much older than Tim is Jason? Somewhere between one and three years, I guess, but I can’t really go beyond a well-researched guess. In my opinion, there isn’t a straightforward answer for this one.
Having presented my facts, here is my conclusion. Jason was 15 when he died. At the same time, Tim was 13. They are two years apart. 
Why? To begin, I’m more comfortable using the number we already have for Tim, 13, than I am dropping him to 12 on the mere possibility that he could have been 12. 
Second, even though The Batman Files (2011) is a terrible source, it does at least sort of indicate that the official DC position is a Jason who was 15 years old at his death. 
Third, visually speaking, Jason looks closer to 15 than 14 at his death. Is that good evidence? No, absolutely not. Comic book art is definitionally variable, but I am going to pull a few panels for you to look over. 
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Batman #427 (1988)
Finally, I feel that Jason and Tim are, in later works, treated as if they are different ages. I’m not going to go into much detail on that one because it is purely a personal reaction, but I would refer to Teen Titans #29 (2005) as an example. That issue has Jason and Tim’s first meeting, after Jason comes to the tower specifically to attack Tim. 
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Teen Titans #27 (2005)
Another well-known issue to check out is Teen Titans #47 (2007).
My basic position is that there are so many ways, all uncertain, to slice Jason and Tim’s ages that I can take my pick. I chose the ones that most closely mirror later canon, fall most squarely into the possible range, and feel the most intuitively right. 
They also have the benefit of simplicity, which was very much a factor. 
Don’t agree with me? Fair enough. I think I’ve given you enough information to make an educated judgment, and I’ve also gone ahead and made a timeline in the alternative. In this one, Jason was 14 at death, and he and Tim are only one year apart. 
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In the Alternative
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Cass appears
Having progressed beyond Jason and Tim’s age gap, we reenter simple canon. I hope you’re as pleased as I am. 
Cass was 17 years old at her first appearance, which we can establish easily based on two different issues. Cass first appears in Batman #567 (1999), during an arc called No Man’s Land. At the time, she is working for Barbara Gordon in the aftermath of an earthquake that destroyed most of Gotham. We learn Cass’s backstory through that issue. 
Cass’s biological father is David Cain, a villain, who raised Cass in isolation, never exposing her to a verbal language or allowing any kind of socialization. By comic book logic, her upbringing gave her a near-superhuman ability to understand and anticipate physical actions, as those actions are her only form of communication. 
Cain trained her as a child assassin, then took her to her first kill. Cass murdered a man and experienced, through his body language, the pain he felt at his death. Immediately afterward, she ran away from her father.
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Batgirl #62 (2005)
We know that Cass was eight years old when she killed and ran. We also know that her first appearance in Gotham was nine years after she ran, thanks to Barbara Gordon’s file. 
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Batgirl #1 (2000)
Simple enough. She was 17. How old was everybody else? We find out from Tim’s timeline. 
This next bit will come up a few times. We know that Tim was 15 from at least 1993 to 2003, established by three different issues. We know from Detective Comics #668 (1993) that Tim was 15 during Knightquest, the arc where Jean-Paul Valley was briefly Batman. Barbara tells us in 2002 that Tim is still 15, and Tim turns 16 on-panel in 2003. 
In Knightquest, Tim gets his driver’s license early, at age 15, because Jack Drake is in a wheelchair. I suppose the wording here is ambiguous on a technicality, but I don’t think there’s any significant argument against Tim being 15; if he was only 14, the language would be different.  
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Detective Comics #668 (1993)
Next, in Batgirl #24 (2002), Barbara says she’s “sending a 15 year old” as she reaches for Tim’s com line.
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Batgirl #24 (2002)
We could stop here for Cassandra’s appearance, since that happened in 1999, between the 1993 issue and the 2002 reference. For completion’s sake, however, let’s note that Robin #116 (2003) is about Tim’s 16th birthday. He forgets about it, so his step-mother throws a surprise party. 
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Robin #116 (2003)
Okay, so Tim was 15 when Cass appeared at age 17. That puts Bruce at 39, Dick at 24, and Jason at 17 if you’re counting by years elapsed since his birth. 
Bruce met his daughter when he was 39 and she was 17, in reference to my original question. Cass is 22 years younger than Bruce, seven years younger than Dick, the same age as Jason, and two years older than Tim. 
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Dick is adopted
This one, having already established Tim’s timeline, is very simple. Dick was adopted in Gotham Knights #17 (2001).
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Gotham Knights #17 (2001)
Again, Tim was 15 from 1993 to 2003, and 2001 falls within that range. Tim was 15, which makes Dick 24 and Bruce 39. 
At this point in the timeline, Bruce, a 39 year old, has two adopted children, one of whom is deceased as far as Bruce is concerned. His adopted children are (17) and 24. He has already met two of his future children, Cass and Tim. 
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This is PART ONE. I’ll reblog Part Two onto this post when I wake up, which should be around the same time this posts. 
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