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I’m currently making an oc to ship with Riddler (I’m planning on making them a director/film historian) and I have to ask, how do you think 66!Riddler would be as a romantic partner? I need some headcanon stuff that I can use for inspiration

I'll split this into two sections, one for analysing relationships he has in the series for ideas, and one of miscellaneous headcanons for things he may do.

This will be specifically for Gorshin!Riddler, as I'm assuming this is the personality you're wanting for the ship instead of Astin - but also if you want to send any extra info through about the OC for more specifics, then I can try get some extra parts for that, too.

Everything you need under the cut! (Long post).

Relationship Analysis

It depends on the personality of the character he's with, as it can differ due to this and give somewhat different dynamics!

This being said, in general I'd say he'd be rather a good one - provided he actually likes the person LOL, which I am assuming is the case here (for examples on how he acts around someone who he's not as attracted to but still being flirty toward, see Mousey ("A Riddle a Day Keeps the Riddler Away/When the Rat's Away, the Mice Will Play", S1E11/12) or Moth ("The Ring of Wax/Give 'Em the Axe", S1E23/24). Here he shows some kind of interest but not a full emotional connection (usually due to the fact they annoy him or mess with the plan in some capacity).

When he properly likes somebody, this is usually due to them being like-minded in terms of schemes and/or interests (so films in your OC's case), or just because he finds them super physically attractive right off the bat (sometimes this option usually lacks the emotional depth though, so can be a little harder to work on. See his dynamic with Siren in "Ring Around the Riddler", S3E2).

Actually talking about liking people now, lol. So generally, he fits under one of three main dynamics (but can go in-between, this is just for ease of explaining), which I'll try to talk through using characters and ships I personally like with 66 Riddler.

We'll start with Riddlemolly ("Hey Diddle Riddle/A Smack in the Middle", S1E1/2). Molly is a very strong personality; sure of herself, not afraid to be on the wrong side of the law... a bit of a girlboss, essentially. I'd say for canonical ships in this show, this is the one he seems to feel most strongly for but this is in part due to the tension of them not actually dating (probably best not to when a mob boss has his eye on her too-), but he shows this through compliments and flirtatious actions.

A few that come to mind: "yes, my pretty", "fantastic, pretty lady", and the whole scene were he sort of teasingly goes to kiss her and then doesn't. He also shows concern for her when she doesn't return in the latter episode, pacing and all. If they actually dated, he'd be very complimenting and praising toward her because he knows how strong of a person she is and thinks that deserves to be appreciated, and sees her as an equal enough to take on board things she says, and even carry her suggestions, which could even, in a more domestic sense, mean going out of his way to do things for her (making her gifts - particularly clothes!! he can sew - cooking dinner, etc.); when Riddler gets fixated on a project he cares about, he won't let up and he'll complete it to its fullest. His actions are his love language, and the words accompany that.

For an extra example of how Riddlemolly and this sort of dynamic looks, I have a fanfiction about it here.

Number two! Riddleline (Pauline - see "Death in Slow Motion/The Riddler's False Notion", S1E31/32). This may prove most useful to you as an example because it's directly related to film. Pauline is also fairly strong in personality but she carries her insecurities and is quite shy at times. Not as sure of herself as Molly, but I think that comes from inexperience of being in the whole crime game. Riddler is very supportive of her here. They share the interest of silent films and acting, and that is something that stands out to him. He compliments her too, but not as flirtatiously as Molly, it's in a more casual sense. Even when he's not outrightly saying something was good, it's implied by his tone and body language (e.g/ smiling excitedly when she's about to act, with a "do your stuff!" because he knows it's going to be great and he can't wait to see the result - seeing as he was a director himself in that epsiode, a role in which he feels most comfortable in, but can act himself too, as seen in the same episode).

He shows her physical attention too, but in a more subtle way because again she is rather shy, and he's doing his best to show his appreciation for her in that less-forward way, even when it's slipping in quick moments before he moves onto the next part of his scheme (like when he blows a kiss to her in the bakery scene - he didn't have to do that, but he chose to; he's actually surprisingly considerate lol). There's also when all the goons go in the back of the van, and Pauline makes move to join them but Riddler stops her, playfully squeezes her face, and tells her she can sit in the front with him. I think this is the best example of how Riddler would look in a properly developed relationship.

Thirdly, and people must've known it was coming, Riddlebat. One of my favourite dynamics of his. So Batman's obviously extremely morally correct and sensible and that's such a contrast to Riddler (even though he knows what's right), except he doesn't so mind as much being corrected in this situation because Batman is intelligent, and that's what he would find most attractive about him. Don't think I have to explain the tension between them sometimes lol, (S1E24... also check out Legends of the Superheroes 1979). Riddler feels Batman can't do anything too bad to him, and that's where the teasing comes in. Batman would be more closed-off and awkward and Riddler would play into that, trying to be as close as possible and say as many things to fluster him as he could, not to mention he'd be very handsy, it not really mattering if Batman says he's got work to do because they both know he likes it deep down. It is not explicit Riddlebat, but I have a fanfiction about their platonic dynamic, and at one point Riddler does tease him in a romantically-tinged fashion. Also have, lightly discussed: how much he believes in Batman being able to fix anything, and another of them just interacting.

I could go into more detail with them, or any of these, but this post is not about them, so I'll do it another time if anyone asks, lol

Relationship Action Headcanons

Gifts, he's a gift-maker/giver through and through, and whatever it is, it's going to be crafted to perfection. Can range from anything from a sweet little drawing, to a new clothing item that he sewed himself. Probably things themed around their favourite silent films, in your OC's case.

Dinner dates - they're one of his favourite kinds, but not out at a restaraunt because he is not paying all of that LOL. At either one of their places, because he gets to make food the way he likes it, and it may not be as perfect as he wants to believe it is but it still goes as his excuse to show off that he can do something, which would, to him, seem impressive given that he spends most of his time in prison, abandoned buildings, or the waterworks. Also may put music on in the background, probably record sountracks from his favourite films.

Flowers, he has a very basic understanding of flower meanings and only knows a few but he explains it in such a way that you'd think he were an expert. Usually these are only bought on special events, but if he just so happens to see a flower he knows this partner will like, he's not above just nabbing it right there and then to give to them on a whim.

Poems! As seen in S1E23 (recites a passage that he "wrote (it) himself"), and Legends of the Superheroes 1979 (bargaining with Batman, he claims "I'll immortalise you, I'll write a poem for you!"), he writes! So I think this would be something he'd like doing - but, hide it as he likes, he gets nervous. He knows he's skilled, but he does get a bit of performance anxiety (the same way he gets phone anxiety), when he's not super hyped up. Leading to one of two options: a) he writes it down and leaves for his partner to find, or b) he pretends to be preoccupied and mutters the poem to himself, just loud enough for them to hear in order to appear casual, whilst still get his point across.

Building onto the former point, he may also write scripts for them to run ideas past them as his way of getting more involved. May overdo it without realising and come off as a bit clingy.

Verbal affection - Riddler's strength is in his mind and his words, so he's going to make sure to use things like this a lot, from outright compliments to general reassurance. Also: riddles where they answer ends up being some kind of compliment or flirt.

Physical affection - again, this majorly depends on the dynamic with the other person, as it can range from brief touches (something akin to how he does for Betsy in S3E2), to prolonged holding (more likely if the other is a stronger personality, like Batman).

Can be difficult at times, because he gets so focused on his work that he can forget to help himself, let alone think to remember he needs to interact with someone else. Gets frustrated when things don't go according to plan or things get changed without him being told first. See how this sort of thing may look in autistic individuals.

May clash as times because he does like being in control of things a lot, and with a director, he'd be trying to get all up in their projects with his own imput, not quite understanding its not his project.

With the film historian part, as Riddler himself has his own special interest in film, he'll like this a lot, now that there's someone who knows as much about it as he does, and they can share new information between each other, but he may get a little upset if they tend to know more about a particular subject he likes than he does. Nothing against them, it just feels like his thing.

Will be very flamboyantly flirty, leaning across desks, and the like. Constantly trying to act things out and help with scripts, trying to be involved in nearly everything, as he considers himself a good actor - and he is! Especially with impressions (see Frank Gorshin's standup work, I can recommend some if you need them).

Film references - may plan dates or complimetns/riddles around certain films either of them like and acting out scenarios either for the romantic undertone or just to cheer them up after something that upset them. Sometimes maybe just for fun, but might get upset if he goes to a lot of effort, only for the partner to not be able to enjoy/spend as much time doing it/attend due to being busy with work.

Hope these helped! As I said before, if there's any specifics I can help with, let me know!

#took me ages to reblog this but i got to it!! for riddler i love him we need more art of him #batman series #batman 66 #others ocs #flick #the riddler #gorshin!riddler #riddleflick #stillwaitin76

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