That's the problem with creating timelines and taking older stories into account. Many of them give specific ages or dates for certain characters, so you have to make your timeline line up with that or you contradict it.
Because of the contradiction, it's fun for me to track down the ages.
Btw. here is my current version for Dick. The complete version with the whole family is already nearly 6 pages, which is unfortunately a little bit to long for a post.
Dick Grayson
The information for Dick are extremely contradictory. During the Golden and Silver Age his age was never clearly revealed. It was later retconned that the Golden Age Robin was born in 1928 [1] so he would have been around 12 in his debut in 1940 [2]. That he became Robin at the age of 8 was also introduced quite late when he was already a member of the new New Teen Titans [3,4]. The only proof for him starting at 8 in the original comics are the 8 spanks Bruce gave him at his Birthday, but on the other hand he had 14 candels on his cake and got his own Batplane as present [5]. And in the second version of his origin story he was already called teenaged when he started as Robin [6].
By the time he got is own solo stories he was already in high school [7] and in this series it was later implied that he was around 15 [8], and shortly after the end of the series he was already drive a car in his civilian identity [9]. He stayed in High School during the whole Silver Age [10-16], and in two stories referred to him as being in 11th grade [13,15]. He was probably at least 18 when was going to collage, since he got a draft-card [17] and was 19 when he became Nightwing [3,4].
Post-crisis the age he lost his parents and became Robin varies in the comics from 8 to 12 [18-23] and the official time lines imply ages of 13 to 15 [24-28]. There are also many different dates for his Birthday (November 11th [29], the week before Halloween [19], the first day of spring/March 21 [28,30], March 10 [31]) and the date of the murder of his parents (June 27th [32], July 15th [29], Halloween [19], one day after Mothert's Day [33]). But according to most sources his parents died two years after Bruce started as Batman and he finally became Robin one year later.
It was said that he was around 13 when the original Teen Titans were founded [34,35], but the timelines imply again a higher age [24-28], and that he was 15 when the Titans joined Joren Jupiter and at least 17 when Dr. Light invaded the Titans Liar [34], even if he was already an adult and in collage during the time of the original comics [36,37].
He was fired as Robin and became Nightwing after he dropped out of collage after one [38] or two [39] semesters so he was 18 or 19 and he had his 20th birthday shortly after this in the crisis year when he was already Nightwing [18,40] and he is said to be 21 around the time of Tims appearance [41-43]. When the Titans reformed after the Technis Imperative he was around 23 [44].
In later comics he is usually referred as 20-something, according to one timeline he his 26 around the time “War Games” and “Under the Hood” [28] and near the end of his Nightwing series there is a story which is placed nearly 10 years after his 17th birthday [45] so that he was probably 26 or 27 at the end of this continuity.
In the new 52 his parents died 5 years ago [46] on the Birthday of his Mother [47,48]. Dick was trained by Bruce for 6 month, and was still 16 when he started as Robin [49]. And was said to be 21 when he joined Spyral [50].
Sources: [1] Last Days of the Justice Society of America, [2] Detective Comics #38, [3] New Teen Titans Vol 1 #37, [4] New Teen Titans Vol 1 #39, [5] Batman#10, [6] Batman #213, [7] Star Spangled Comics #70 ,[8] Star Spangled Comics #122, [9] World's Finest #66, [10] Batman #162, [11] Batman #166, [12] Batman #192, [13] Batman #202, [14] Detective Comics #380, [15] Detective Comics #386, [16] Detective Comics #390Ƈ, [17] Batman #217, [18] Secret Origins Vol 2 #13, [19] Secret Origins Vol 2 #50, [20] Nightwing Vol 2 #73, [21] Nightwing Vol 2 #76, [22] Batman Confidential #13, [23] Robin Year One #1, [24] Batman - Secret Files & Origins, [25] Nightwing - Secret Files & Origins, [26] Guide to the DC Universe - Secret Files & Origins, [27] Teen Titans Vol 3 #0.5, [28] Nightwing: Year One TPB, [29] DC calendar 1976, [30] Robin Annual #4 ,[31] Batman - The Silver Age Newspaper Comics Volume 2, [32] Nightwing Vol 1 #1, [33] Batman Dark Victory #8	, [34] Secret Origins Vol 2 Annual #3,[35] The Titans Vol 1 #16, [36] Teen Titans Vol 1 #25, [37] Teen Titans Vol 1 #44, [38] Batman #416, [39] Nightwing Vol 2 #42, [40] New Teen Titans Vol 2 #18, [41] New Titans Annual #5, [42] New Titans #71, [43] Deathstroke Annual #1, [44] The Titans Vol 1 #5, [45] Nightwing Vol 2 #134, [46] Batman Vol2 #0, [47] Nightwing Vol 2 #0, [48] Secret Origins Vol 3 #1, [49] Batman and Robin Annual #2, [50] Secret Origins Vol 3 #8
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