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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.
Now I'm going to set some rules. I will be talking about their history/interactions/relationships. I will be skipping a few areas here and there since they don't lend much to be noted ("City of Bane" I'm looking at you).
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.
Rather instantly Tim is quite unnerved and spooked at Cass (compared to Babs and Jean-Paul) that the newest Batgirl was raised to be an assassin. You can tell there's hesitation via Tim here, but this doesn't really get expanded on until near the end of the NML event.
Robin #73 this is expanded on, as already we've seen Cass team-up regularly with Jean-Paul, but this is the first time Tim is with her as she's his "guardian bat" as he's rescued (a long subplot involving Tim/his dad pulling heaven and earth to get his son out of there).
Also, I can't help it I love this cover. There's just something hilarious that this is the picture Tim's dad gave to the government and is plastered EVERYWHERE.
The issue is rather weird though, as Cass's costume has a tattered cape for one, and two her bat symbol is completely yellow save for the bottom panel. But yeah, Tim is creeped out by Cass, and is standoffish.
There's another point where again Tim views his uneasiness with Cass, but she still respects his wishes.
Things do go wrong with the extraction as several remaining gangs try to nab Tim, thankfully the guardian Bat saves him and Tim's taken back to see his father.
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.
It isn't until surprisingly Batgirl #18 where it all comes to a head (for the most part) as a case pulls of them in.
It isn't long in their little venture before Tim's freaked out again by Cass's move set. Yes Tim, she can dodge bullets. Practice harder man.
Again Tim is of very quick words as he gets the heck out of dodge leaving Cass all, "da hell?" Thankfully, the case they're both on leads to the both of them accidentally running into one another.
You just gotta love these little glimpses of the chemistry the two have when working together as both tackle the thugs with quite ease and the moment an innocent life, Tim drops the uneasy he has with Cass, and the two are one. Somewhere Bruce is smiling.
This all leads to Cass confronting the one-off villain for the issue, Deadeye who has a cybernetic eye that allows him to pull trick shots. So a third-tier Deadshot basically. Though I believe this is the third technically "meta" character she's confronted.
And now we get an alternative take with Tim with his back turned as Cass addresses her wounds. But Tim turns to peek and for the first time as a reader we're told of the various scars Cass has across her back she got due to "training".
They get back on the case, and you just gotta love the expressions artist Damion Scott put in this issue. Even though Cass's face is covered, damn is she so expressive. As well again Tim's scared by both Cass's "Batman impersonation" and the criminals will kill the hostage.
Short version, the duo (okay Cass does most of the work here taking down Deadeye with ease) and this time leave on good terms.
The thing though I've noticed throughout both their runs is that even though they leave on good terms here. The two then team up again in Harley Quinn #10-11 when Harley decides to start cosplaying as Babs as Batgirl and Tim runs into her first.
Let's be honest, Tim probably deserved that kick to the stomach regardless for accidentally outing Cass's first name prior to this. Something which Harley then uses to her advantage to unnerve Cass.
But it can only work so much as Cass does get the upper hand eventually. Still, it does lead to this sweet little moment between the two watching Dick/Babs.
The next time Tim shows up in Cassandra's life is well the Bruce Wayne: Fugitive event as Cass/Steph goes on the case to clear Bruce's name. They present the first clear evidence to the family, and well you know that story. Just read the Cass/Steph stuff.
Tim does show up in #27 and #29. But-- yeah this pertains more to Cass/Steph or Cass/Dick than Tim and her.
It isn't long before Tim does show back up in Cass's comic as both he and Steph pop in for #31-32. I covered this in the Cass/Steph retrospective but yeah Tim/Steph get caught up in an adventure Cass/Connor Hawke (Green Arrow) are having with a cult that is targeting Tim's pop.
It hits me though that this is the final time Tim (along with Steph) appears in the Puckett/Scott run, but even here this arc was written by Chuck Dixon. So neither get their proper sendoff in this run with Puckett (well I guess Steph does more than Tim).
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.
Now it's time to talk about the glory that is Superboy Vol. 4 #85. Aka the first time Cass/Kon meet and Tim is the straight man to it all the antics going down.
Like literally, the three of them just banter so well. I'm kind of surprised DC didn't turn this into a thing cause damn do they work well all three. Also Tim you are such a dork trying to pull a Batman here.
Literally, both Cass/Tim's reaction to standing up against Batdad is glorious.
I still crack up at the Pig Latin and Cass giving a look like, "Seriously you're willing to take the punishment Batdad gives? Truly Conner is a SUPERboy." Just track it down if you can of this issue given the chemistry of all three is glorious here. Pity this is all we got.
I'm gonna assume that these next portions take place around this time period as well in Gotham Knights #42-50 all over the place. Aka the infamous issue where a social worker finds Bruce, Tim, and Cass like this. Um yeah...
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.
Though Cass's solution to dealing with the social worker is quite inspired.
And we get another family moment again with this.
And we get a moment where probably somewhere Lady Shiva is smiling at the way her daughter is handling things here.
But these are all just amusing family moments with everyone. The next little crossroad where Tim/Cass meet is Robin #119. It's a rather complicated plot. Just that Tim is told that in the future someone in the Bat-Family will turn rogue and well Tim has to figure out who.
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. 
So Tim is at somewhat odds at what he originally believed with Cass and what he currently believes with her. He goes with the assumption that anyone in the Family can be a true suspect. Don't ask who it was, I just follow the Cass. 
Batgirl #45 is probably the first issue where Tim/Cass have a Dick/Babs moment. It's kind of-- there. But then again Cass's protective tackle as she did it to Alfred in this run too.
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.
Now I looked at all the stuff going on up to this point this all rather. 
Cause you see what's going on in Gotham Knights and Superboy yet here we get a tease of interest of Tim looking at Cass in a not so sisterly light. Yeah....
Cause you see what's going on in Gotham Knights and Superboy yet here we get a tease of interest of Tim looking at Cass in a not so sisterly light. Yeah....
Tim does show up in #50 too but really to help both Cass/Bruce who are doused with a new variant of the soul drug. It's a cute little moment of interrogation, but it does show how much Tim cares for both the two.
But really the next big juncture between the two really evolve is in the "Fresh Blood" crossover the two comics share from Robin #132-133 and Batgirl #58-59.
I'm gonna call it a night and try to finish this tomorrow. I apologize just that there is gonna be A LOT to cover tomorrow and this feels like the perfect "intermission".
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.
While it's about time that Loeb gave us something with Cass (0 appearances in Hush event), sadly this is about it. And I can't help but be all below with this. You're supposed to be promoting these characters and-- if you aren't fond of one. Well, why are you here then?
The "Fresh Blood" crossover between both Cass/Tim's comics was a crossroad for both characters. For Tim, it was right after DC smacked him with TWO tragedies (losing his father in Identity Crisis, Steph in War Games) and for Cass DC began neglecting the character more.
It was also a turning point for both in regards to the other as well. Because of up to this point, the two did team up (as shown), and were friends. But this is when their bond began to tighten and deepen. Though Bruce pushed both out of Gotham I think he knew both needed this.
Because this is the x-over everything is built on what comes later. The bad (I really have to talk about it don't I? given it bridges both), the ugly (must I talk about it?), and what good we got with Cass in the future years.
With the story itself, both characters are working on this new status quo. Tim? He's all himself on this. Plans within plans. Pages with pages explaining how he will handle this (but I'm just posting one). Cass? She IS the plan and just needs one page.
But early on, you can tell Tim falls back on his old habits with Cass. While he says she can stay, he slams the door not wanting to open himself to her. While Cass, can clearly tell he's hurting, cause she is.
The very next day (after probably one of the best moments Gabrych had in the run of Cass trying to read), Tim greets her with tea, but resistant to talking things out with Cass. Still, the gesture is nice.
The two meet the two contacts from Bludhaven, and we get a really nice moment where Tim is inquiring while Cass watches then realizes (due to their body language) that something is amiss. I kind of wish we saw this more with Cass.
So, the two go-to location to find "Blockbuster" still under a slight case of death and Penguin running the Bludhaven underworld now (and where we switch to Robin and glorious Damion Scott art).
There are three things to assess from this page. #1 Both know Penguin is being overtly cocky and find out why. Tim is freaking out because (well fighting isn't his thing) #2 Cass is so much like Batman in this. Calm. Cool. Collect. Taking all this in.
#3 War Games.. epic? Um no. NO!
The moment she see's an opportunity she starts a ruckus of the two of them vs. the entire Bludhaven underworld. Tim is just trying to stay alive, while we see his pov on how he views Cass fighting during all this.
It also shows her Batman side. She's got that Batman edge of being a surgeon when it comes to fights (even more so). Which is perfectly captured by the glorious Damion Scott art.
But pure skill can't help them alone, and eventually, the numbers/dirty tricks (i.e. Penguin using a gas goon to fill the room with gas) finally subdues both. But at the very least this is a worthy way of jobbing. Taking A TON of foes down before going down herself.
Still, even with our dynamic duo down, Penguin can't help but get his pocket full of more money to profit on who gets to unmask the two while the two recover. Which leads us to this...
Well, this is a crossover and comic rules dictate the two sides must have a tussle because these are the crossover rules. Even if they are friends. Least all the mobsters know who to bet on in this. Sorry Tim...
The thing that I find fascinating is in Tim's parts of this x-over it's all about the plot with the Bludhaven underworld and Tim's mindset with some hints. While in the Batgirl halves are Tim/Cass period with everything else below it all.
Anyway, the REAL meat and potatoes of this x-over is the finale in #59. Cass vs. Tim. Where this little "play" they put on feels more with the words they keep throwing at one another are sharper than the blows.
But let's go to that later, let's take in the words. Tim reveals he moved to Bludhaven to get away, but instead Bruce sends Cass to be with him. He wants to cope with his grief alone and just be alone from this life. The emotional outburst allows him to "win".
Cass appears dead, from Tim's attacks but Penguin being smart for once hands Tim a gun to make sure she is. Tim pulls the trigger and well I think this is where I realized, "Huh Gabrych knows his Puckett." Nice. The two then escape Penguin's clutches and deal with the aftermath.
And once again we're back to #58 with Tim struggling and being quiet. Keeping his pain within himself and Cass sees it screaming with her ability.
I digress this is probably the most of where shippers of the two have in this issue. With the way they act here, and Cass's own dialogue in her narration bubble. "she was his girlfriend. that other girl. He had feelings for her too." And then comparing she's never had a bf.
There's just something-- here. A spark. Going back now seeing the Gotham Knight stuff prior to it (acting brother/sister) long with the stuff later on, and how cliche ( later used in TT OYL between Tim/Cassie) now has me all 
.
.
Still, the two begin to work out their differences when Cass looks to their "fight" and the words Tim told her. Tim explains why he told her this. Something that is brought up later by Oynx. Tim wants a life outside the Family eventually, while Cass WANTS to be the next Batman.
There are the methods too as Tim doesn't like Bruce's approach (from War Games), while Cass does. But they agree on one point, they will work together when needed, but each will have their own way of approaching Bludhaven. Which Cass's inner Batman is screaming, "YEEEEESSS!"
That and they make quite the team when together. Each balances the other's weakness and strength. Sadly we only get two mentions (that I know of) with their stay in Bludhaven together. The first is this passing moment in Tim's comic.
Which I just find adorable that Cass sneaks in to steal all of Tim's hot water, and then takes his rice crispies. It's such a sister thing to do.
Then there's this little tale in Batman: Allies & Secret Origins #1 which has a story by Gabrych that deals with Cass/Tim having one more adventure in Bludhaven together which begins with Cass training Tim (hmm.. this situation feels awfully familiar).
And yeah it quickly goes that route with both their hearts still broken at the loss of the mutual loved one.
It again goes with the two of them having a disagreement over Batman's methods. Same as before. Thankfully a silent alarm is triggered the two respond and deal with. Cass kind of knocks them all out as Tim notes their hardware hints at more, so now he teaches her.
Tim proves his point as the news reports that, and we get um a War Crimes lead-in. But yeah there is one other "alternate universe" tale of the two also shown around this time period too.
Solo #11 which is a Damion Scott spotlight, and the creator admits where the two might be leading towards (if we don't take into account what actually happened). Yeah... to this I kind of by it for the issues on Batgirl and Robin with this. Everywhere else and the future um..
But yeah this future tale has Cass dyed her hair red (in homage to Babs) and yeah. I still love the tale for what it is, Cass is Batman and she's happy with someone. I mean it isn't Steph, but still. Plus we got Cass/Steph too earlier in this issue.
So yeah, this little era probably is kind of the reason this sort of ship between them exists within some fans. Because at the very least it feels more justified. Because.. um..
I have to talk about the elephant in the room now, don't I? Yeah, we reached that point. Ugh...
Yes, we come to the juncture which will be hardest to talk about-- Robin OYL #148-151.
So let's start with a word from Tim that many themselves will utter repeatedly when going into this story.
Small interesting sidenote now about this story only one editor is still with DC from this creative team and is currently writing Detective Comics. Everyone else has left the company since if on good terms or been fired.
