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There is one appearance that takes place prior to "Fresh Blood" with Batman & Superman #5. It has Cass/Tim a tiny cute nugget before Loeb proceeds to have the entire Bat(and Super)-Family job to Lex.
It just goes further with Tim confirming what Babs says earlier that putting on "this costume" makes guys look at you in a different way. Well, that different way allows the drug-possessed rioters to one-shot Tim.
Dammit, Twitter why are you focusing on that area of Tim?! Ya darn pervs! Anyway, suspect #1 is Cass and Tim goes over the reasons as to why. Geez! If only this was actually applied for later on. It would have gone down better. 😐
And we get a moment where probably somewhere Lady Shiva is smiling at the way her daughter is handling things here.
There are various subplots (Alfred is sick, there's a social worker, Bane, Man-Bat's kid, two other main plots) at play here but there are a few cute moments of the Family like this. So brother/sister the two are acting here it's cute.
Still, there's some good banter and the four work well in taking down the bad guys (they never had a chance). Tim still gets the final word in the arc as we learn the fate of the McGuffin the villains wanted so badly.
So not soon after, Batgirl vol. 1 kicks off, and Tim does make his first appearance in the comic with #5 as Bruce is trying to figure out the origins of a tape he was given of a young girl murdering someone on film.
So with that said, I'm going to start in Batman: Legends of the Dark Knight #120. Yes, the very issue where Cass becomes the new Batgirl is also the first time Tim/Cass interacted and it is the seeds to where most of the first few years of their interactions lie.
So in another entry of interactions/history/relationship with other characters Cass has had. I'm going to cover the other major being in Cassandra's life (other than Stephanie), one Timothy Drake.
When you wake up to find there's not only a new issue of DCeased: Hope at World's End, but who are in it.