The rules are simple. Name two characters who haven’t already met or have heard of each other before.
Could even be from the wider multiverse to allow people to get as creative as possible. So Wildstorm, Milestone, Young Animals, etc.
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Harley Quinn and Hitman
Poison Ivy and Natt the Hat
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My first pick would be Enchantress and Hardware
I love both these characters and one of their personality quirks are being known jerks. Even when Enchantress is a hero, she’s incredibly sarcastic and mean-spirited to others, while hardware doesn’t really make it a mission for people to like him. They hate authority figures and are people who take themselves way too seriously.
Whenever they had protégés. Curtis and June make nothing easy for them and are tough teachers.
Even though they come from entirely different worlds. Tech and magic. I still imagine both would find common ground and become solid allies.
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Always trying to bring up Hitman, eh? 
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Has anyone wanted to see Mongul and Despero meet? I don’t think neither met yet but wouldn’t it be cool to see these two maniacal evil warlords, after trying to kill each other, become best friends…
I hope it would be like this
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I got another one…
Ryan Wilder Batwoman and Jace Fox Batman.
It’s actually crazy how similar they are to each other. Both are African-American superheroes who stole a bulletproof bat suit. Both have a criminal background and have a complicated past with authority figures to not trust them all that much.
Both have modified said Batsuit to show their different and “represent” people like them.
Both are woke as heck. Making social justice a vocal point of their vigilantism. Both have association or are adjacent to the Batwing character.
Their personalities are slightly different but not by much. Ryan is more casual while Jace is more contemplative. Ryan grew up poor to only later become the CEO of Wayne Enterprises and also found out she was the daughter of a wealthy family. Meanwhile, Jace lived for most of his adult life pragmatically and avoid the wealth of his family for years until he decided to become Batman and took advantage of that wealth and resources to be a vigilante.
They aren’t my favorite characters(actually kind of annoyed by them 
) but I obviously know enough about them and what they are to see how if they ever met, both would actually hit it off quite well to become best friends.
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Alan Moore worst nightmare about vigilantes: Rorschach
Alan Moore best case scenario vigilante: V
Sure they are complete polar opposites yet share a strong moral code with a tendency to get crazy. Maybe that could be enough for a odd friendship between these vigilantes.
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spoke and batman
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This one is pretty good. the idea that comes to my mind is misery loves company. The kind of dynamic I see these two having is moody and meditative. Two tragic superheroes that have lost their humanity could find a sort of cosmic existential connection if they ever met.
Eternity Girl(Caroline Sharp/Chrysails)
Breach (Tim Zanetti)
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This is a tough one…
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