Headcannons!

Chapter 1: Kids!

TWO-FACE/GILDA DENT: DEXTER & DUELA
He cannonly had a daughter named Duela (well... Okay technically not him, another universe female version of him called Three-Face, who was with Joker, but same difference), and in multiple versions he had an ex wife/fiancée, some of which she died when he got his scars. Anyway, I think it would be interesting for him to have kids. And, of course, he would have TWO. Likely twins. And, you know, he did have the whole 'perfect life' thing, amazing lawyer/fiancée/running for something-or-other/friends with Bruce Wayne the billionaire. Having kids would kinda add to that white picket fence vibe. he also had boy/girl twins in one version (the version was the one where Bruce's parents are Batman & Joker, and was pretty Fucked up), I don't like most the things about their story, but DID like some things about the boy twin. He name in-canon is Dexter Dent, but I will change it once I figure out a better name for him.

Welp, nope. Somehow I fell in love with the name Dexter. It stays.

RIDDLER: STEPHANIE BROWN (ADOPTED) (NIECE), MOBY KROW (SON)
He worked with her father, her father was basically just more-evil him, they have the same thing pretty much, he is a ❓ and she is a ❗ . Anyways, yeah, I think he would adopt her. Plus then she can be with Tim without kinda being with her adopted brother. The son... 2005 Riddler. Look it up. You'll understand. Moby Krow is not his actual name, he changed his name to it when he came to Gotham, to meet his father. Moby Krow is a scramble of Bookwyrm.

Okay, slight edit to this: Stephanie is his niece, not his adopted daughter. He worked for his uncle (Cluemaster) when he was younger, and occasionally babysat his niece (Stephanie). When Cluemaster died, Edward took in Stephanie. Here's how they are related:

Mark - Riddler's father

Mark - Cluemaster's cousin

Cluemaster - Riddler's uncle 

Cluemaster - Stephanie's father 

Riddler - Stephanie's uncle

Moby - Riddler's son 

Moby - Stephanie's cousin

JOKER: CREEPER (ADOPTED)
I just imagine Creeper accidentally falling into the vat of chemicals, Joker pulling him out, and Joker panicking when he learns this kid is now a more-insane him, taking care of him and accidentally adopting him. (Oh, my Version of Creeper is a teenager).

PENGUIN/CATWOMAN: KATRINA {CATGIRL} {KITTYHAWK}, KATHRYN {CATGIRL} {WILDCAT}, ADRIEN (SON) {CATBOY} {CAT BLANC} 😏, HOLLY {PUFFIN} {SONGBIRD}.
I didn't ship them. I saw the ship. The ship slowly sailed into my brain. Now I shippity-shippy-ship them. Don't get me wrong, I love Catwoman, she is an amazing character. ...she is also 💯 a gold digger. Her marrying a mob boss makes sense. Plus, they are pretty much the only non-insane rogues so... Also, comment if you get the Adrian reference! Katrina wears a pink and black outfit. Kathryn wears leopard print, and shirts with cats on them (when in civvies). Adrian has electric taser guns, and black hair, he wears white when in uniform. Holly wears purple, is a singer, and works as Penguin's sidekick.

JONATHAN/LAB?: PHOBOS (DAUGHTER), DEMOS (SON)
~Phobias and Demons~
Tell me I'm wrong. Tell me he wouldn't name his kids this! He was old enough to be a psychology teacher, he definitely had kids. I think Phobos would be older, but both would be mid-older teens.

MAD HATTER: ??? (WHITE RABBIT), ??? (DORMOUSE)
I'm not sure if he would actually have kids... But I like the idea of his kids being Alice-themed villains/heroes. Plus his whole literature thing would work with him having kids. Him just reading the book to them, or having to deal with the movie because they are obsessed with it.

HARLEY: JESSIE (SON)
Eh, the name matches, and... Okay, I don't have much for why this works. But I think it would be cute. He would be a baby, and one of the youngest of the rogue-kids. Maybe hers and Jokers? Or someone else? I can just see her taking time off supervillaining while she is pregnant (and Batman agreeing not to capture her as long as she doesn't commit any more major crimes, for this period of time), then trying to figure out how to be a mom (asking ALL the other rogues for help).

IVY: OAKLEY (A SON!) {POISON OAK}.
Her having to get over her hatred of men, because she has a son? YES PLEASE! Also, him following in her footsteps, becoming Poison Oak? I think it would be interesting. I don't know who the fuck the father would be, but I think it would be interesting to see her as a mom.

MR FREEZE/NORA: SNOW (GIRL)
Okay, wouldn't it be more interesting if Victor and Nora had at least one kid before the accident? It would add more to his story if he wasn't just trying to save his wife (an already noble cause), but also the mother of his daughter. It would also make sense for how devoted he is to Nora, if they've already started raising a child together. Besides, they clearly won't be able to have kids once she is saved (he's in a cryostasis suit, plus I'd say their biological ages would be around 40s for Victor and 30s for Nora, which is kinda dangerous to have a kid at...) so making them already have a kid would make more sense. Plus, seeing Freeze be a dad would be adorable 😍 imagine, him being all cold and stoic, then Snow tells him she's upset about something, cue SNOW DAY! I think it would just be really cute! And he deserves some love in his life.

Chapter 2: Siblings!

HARLEY & HARVEY: They have matching names. Okay, so what if they are siblings (or half-siblings), and Harley changed her surname when she became a psychologist at Arkham, because her patients wouldn't listen to her if they knew her brother is the one who put them away. The idea started off just as a joke because of their names, but now I actually really like it. Also, they both have high-up jobs working with criminals, and both have mental issues. 

BRUCE & SELINA: Okay, okay. I know! But hear me out, what if their flirty thing is replaced with sibling banter? They would know how to push ALL of each other's buttons, and it would give a similar reveal: learning that his sister is Catwoman, a supervillain? Anyways, I feel like it actually makes sense. Their parents die, he leaves Gotham, she stays. Maybe she gets taken in by Sewer King? She becomes a thief, blaming the corrupt rich of Gotham for her parent's death. You honestly wouldn't have to change all that much. They even have matching themes! Tight, black & yellow, Cat/Bat suit. I think it would work well for those who ship the characters with other people (like her with Penguin, or him with Joker), and still want to keep their dynamic.

CLOCK KING & MAD HATTER: This is actually cannon to one old comic (Batman 66' I believe). they both have similar mental issues, they are both English, their themes also kinda match. I can see Jervis (MH) calling Temple (CK) 'White Rabbit', for his whole time thing.

They have different surnames because Temple got married and changed his name.

PENGUIN & NORA FRIES:
okay, so, I used to headcanon that Mr Freeze and Penguin were siblings (because of the shared cold thing), but then I had another idea... What if Nora and Penguin are? It would make sense why he funds Freeze's work, he's trying to save his sister. Also, Nora's cryotank could be kept in the Iceberg Lounge, in it's cold rooms. Victor And Nora could have chosen their last name (Fries), because of a shared love of the cold between her and her brother (Oswald). Also, (according to some things) they were born around the same time. I think it would just be really interesting if they were siblings.

Chapter 3: Dating!

PENGUIN & CATWOMAN (MARRIED)
For the reasons I said earlier, they fit. I feel like most people wouldn't know they're together, and they keep their own last names for business reasons, but they would actually be a really good couple.

MR FREEZE & NORA (MARRIED)
Anyone who thinks otherwise is insane, no offense.
#VicNora4ever!!!! 🩵🩵🩵🩵🩵

BATMAN & JOKER (DATING)
In a universe where Joker's evil is toned down (and he didn't purposely kill any of the bat-kids) I think they would work. Joker is already cannonly in love with Batsy, and I think we can attest to the RAINBOW BATSUIT for why they go together.

HARLEY & IVY (DATING)
Ivy literally have her the antidote to her poisons so Harley could stay at her greenhouse. They lived together for a while. Harley is the only human Ivy cares for. This is cannon too. Plus they just look sooo cute together.

SCARECROW & MAD HATTER (DATING)
Wizard Of Oz & Alice In Wonderland? YES. Jervis sings Alice quotes, and Jonathan sings nursery rhymes. Jervis is a bowl of sprinkles, and Jonathan is a brick of dark chocolate. They fit.

RIDDLER & TWO-FACE (DATING)
I don't know why they work, they just DO.

BABYDOLL (CLAYDOLL) & CLAYFACE (DATING)
Okay, so what if the same thing that happened to Clayface happened to Babydoll, turning her into Claydoll, freeing her from being forever stuck as a child? I think, if that happened, they would actually make a pretty good couple. They are both obsessive actors... Pretty much that's the whole reason I think they would work.

DICK GRAYSON & BARBARA GORDON (DATING)
I don't have any other ships for him, and they work so...

JASON TODD & DUELA DENT
I just think they would make a pretty good couple. Plus, I can't see Jason dating a non-criminal.

STEPHANIE BROWN & TIM DRAKE (FLIRTING)
Stalker meets Genius detective. Way to much coffee Glitter bombs and . Hero and Criminal. Third robin and only robin ever to be fired. They work! I feel like as teens they would be really flirty towards each other, and would only get together as adults.

DAMAIN & JON-EL (FLIRTING)
Jon - 'You have a cow?'
Damian - 'Of course I have a cow!'

Superman - 'Another traumatic moment might unlock more powers.'

Damian, smirks - 'Lets test that theory' pushes Jon down long hole.

Damian, sees bruise on Jon's face and Bully walking over - 'Oh! He hit you! - quietly - 'Should have used heat vision on him, honestly.
Damian, chi blocks/paralyses him.
Jon, horrified - 'What did you do!?'
Damian, smirking - 'A trick I learned from my grandfather. He'll recover... In a week.'

CASSANDRA CAIN & SEWER KINGDOM KID (FLIRTING)
Cass is mute (or doesn't speak) and uses sign language. The Sewer Kids do the same. I headcanon that she (and Damian) spent a few years in the Sewer Kingdom, so I think she would bond with someone there?

IVY & TWO-FACE (EX'S)
He destroyed a rare species of rose to put up a building or something, so she seduced him (to the point where he was gonna propose), then she used part of the last one of those roses to make poison, put it on her lips, then kissed him, attempting to kill him. This is all cannon. She would give a begrudging half-apologize, and he would kinda-not-really forgive her, because Harley told them to.

JOKER & HARLEY (EX'S)
In my version he isn't abusive, they just both realized they like other people and break up. They are the kinda people who act like they are together without meaning to. A rare case where the breakup is 💯 mutual.

TWO-FACE & GILDA DENT (EX'S)
I needed a mother for his kids, so....

Chapter 4: Timeline!

February 19, 1974 - Bruce Wayne was born.
February 19, 1974 - Jack Napier (Joker) was born.

June 5, 1974 - Harvey Dent was born.

December 7, 1974 - Victor Volkov (Fries) Was born.

March 14th, 1975 - Selina Wayne (Kyle) was born.

April 1, 1976 - Edward Nashton was born.

May 31, 1976 - Oswald Cobblepot was born.

May 29, 1977 - Nora Cobblepot (Fries) was born.

June 26, 10:47 PM, 1984 - Selina & Bruce's parents were killed.

March 20, 1992 - Dick Grayson was born.

August 16, 1994 - Jason Todd was born.

February 2, 1996 - Dexter Dent & Duela Dent were born.

October 28, 1997 - Riddler's son was born.

July 19, 1998 - Tim Drake was born.

July 5, 1989 - Bruce left Gotham, and started his training.

March 10, 1999 - Bruce returned to Gotham, and started becoming Batman.

December 31, 1999 - Victor Fries & Nora Fries got married.

January 5th, 2000 - Damian al Ghul & Cassandra al Ghul (Bruce & Talia Al Ghul's children) were born

October ???, 2000 - Snow Fries (Victor & Nora's daughter) was born.

???, 2002 - Dick's parents died. Bruce adopted Dick.

???, 2002 - Dick became Robin.

???, 2003 - Bruce Wayne adopted Jason.

???, 2004 - Nora's accident, Cryostasis (age 27).

???, 2005 - Victor's accident, Cryosuit (age 31).

???, 2005 - Victor became Mr Freeze.

??? (Early), 2006 - Dick passed the title of Robin to Jason.

November 1, 2006 - Jason died.

March 3, 2007 - Tim became robin.

???, 2007 - Damian & Cassandra left the League Of Assassins.

???, 2007 - Damian & Cassandra were taken in by the Sewer Kingdom.

April 1, 2008 - Jason came back, and became Red Hood.

???, 2009 - Bruce met Damian & Cassandra.

???, 2009 - Damian became Robin. Cassandra became Bat Girl.

???, 2010 - Cassandra became Gargoyle.

???, 2012 - Dick moved to Bludhaven.

Chapter 5: Other

TIM IS RED-MITE!
Okay, so what if Tim Drake is actually Jason Todd's Imp? He is a stalker, and he literally named himself Red Robin (Matching Red Hood). Also, Mite backwards is Etim. eTIM.

Timothy Jackson Drake

Jason-Mite Koch Ty Dark