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.