Best way to go about writing a hero/villain romance

Really, that's all this is about. I just thought I'd ask what you all think is the best way to orchestrate a convincing romance (one of mutual attraction) between a hero and a villain. Examples would be nice if you have any, and any other writers who are interested in the topic like me are encouraged to bring their own questions, samples, feedback and anything else that's relevant to this thread.

This sounds really interesting. Do you have any ideas already, or did you just think of the concept? There are several ways to do this. With a male hero and female villain, there is always the High-Heel–Face Turn. Silverbolt and Blackarachnia of Beast Wars are a good example of this, because the female actually keeps her characterization as a Femme Fatale even after she switches sides. For a female hero and male villain, there is always All Girls Want Bad Boys, but if not done right it won't be able to last and can lead to Unfortunate Implications if the relationship becomes abusive. Personally, I think it's more interesting if the male villain is an Anti-Villain or a Well-Intentioned Extremist. An example of this is Shakugan No Shana and Sakai Yuji, where in this case Yuji is a case of The Extremist Was Right.

I've actually thought it would be interesting if a female hero had a relationship with an Evil Overlord and had his child, then left with the child and both became part of La Résistance, thus the child would actually be the legitimate heir of the Evil Overlord despite being part of La Résistance.

Oddly enough, one of my favourite examples might be this Super Stupor strip.

I think the best hero/villain romances might be based on something more than just a physical attraction. Maybe they make each other laugh with their quips during fights. Maybe they get into spirited philosophical debates. Maybe they both start singing along to the same song playing on the radio during an encounter.

I can't think of any examples offhand of this type of thing.

I would say that this depends very much on the nature of the hero and villain, if that makes sense. Let me elaborate a little:

• Say you have a Hero(ine)who falls in love—not with the Big Bad himself/herself but someone on their side. They may have to keep their relationship a secret so that the love interest's evil boss doesn't find out. And what if others on the bad guy's side discover it? Will they keep the secret out of Villainous Friendship or will they turn over their knowledge without hesitation in order to ascend the ranks, settle an old score or just For the Evulz?

• If the Big Bad and the hero(ine) fall in love, then it's a little different but the same. The protagonist obviously has some problems with this guy/girl and they will have to be sorted out. Does the good guy decide to ignore or even go along with the Big Bad's plans out of love or is it the other way around? Does the villain see the error of his/her ways and leave the path of evil behind?
  • And what about the hero's friend's or the villain's minions? What do they have to say about this? Do the hero(ine)'s friends warn him/her off or try to finish off the bad guy to "protect" their friend and think something along the lines of "he/she'll thank me later"? Do the bad guy's minions take advantage of the relationship to topple their boss and gain power for themselves?

• These are just a few ideas, all of them are something to think about when going about creating a hero/villain romance. I hoped that helped.

I get annoyed at the female villain falling for the hero and so turning away from the "evil" side, and also at the genderflipped version, the latter especially if it's played up as ~true love~ or ~romance redeems~. I could be amused if the super-charismatic villain successfully seduces the hero to the dark side. (If the villain is actually a justified antagonist I'd rather the protagonist realise that without the involvement of romance though.)

As for believable... well, if the hero's supposed to be a good person, then there's an upper limit on how terrible the villain is allowed to be. For a good person, massacring villages should definitely be a huge turn-off. The bad things the villain has done should always be kept in mind, if the hero is actually a hero; of course, you could have a flawed character if you wanted. Even then as the writer you should keep this in mind because you should know this is the choice you're making. If the villain and hero treat their conflict as a game and start flirting through it, then I'd assume the effects of the game don't matter to them, and if people are hurt then that portrays the hero as callous.

Assuming this goes beyond mere attraction/infatuation, the villain needs more than charisma and good looks; the hero and villain need to be able to relate somehow, in a way that's important to them, and they need to be able to discover that about each other. If it's basically "oh no he's hot" then... the hero'd better get over that quickly.

It may be plausible to go for a redemption arc depending on plot, and the resolution isn't the defeat of one or the other but both of them coming together to build a future for themselves or whatever. Those go a bit more for emotional catharsis than hitting a fetish, I think. It's strongly dependent on what these characters are a hero and villain of—what are they fighting for, and why?

Got two supervillain/superhero couples.

First is an old school The Cape and a highly self-centered villain. They both like eachother, and are willing to admit it to themselves and eachother, but they can't reconcile their alignments. The hero is like I said The Cape, who believes in Good Feels Good and all that jazz, whereas the villain wants what he wants doesn't mind threatening or hurting people to get it.

Second is a more pragmatic guy. Mainly a hero because it's just a really neat idea, not out of any inherent sense of justice. The villainess is a bit of a ditz, but rather unstable, with her primary Berserk Button being women who comment on the fact that the hero (who she definitely totally does not like. Really. For real.) is handsome. Both like eachother, but neither is willing to admit it, despite it being plain as day to anyone who sees them together for five seconds.

Tried coming up with some ideas on how to move them forward. Best I could come up with for Couple 1 is the hero suggesting they both give up the super biz and settle down, which of course the villain rejects out of hand. So then I thought, just clandestine lovers, trying to convince the other to come over to their side. Which is kinda boring, so I have no idea on that one.

Couple 2 remains mostly the same throughout; even if they finally admit they like eachother, there's still the problem of her Berserk Button (emphasis on BERSERK), so they'd still end up fighting one way or the other.

You might want to try having the "villain" be "evil" primarily for ideological reasons; The hero is a true-blue American patriot, and the villain is a Soviet supersoldier, for example. That allows them to do Enemy Mine against really evil people, and perhaps they can finally get together when the political climate changes.

I mostly have solved it by establishing boundaries, like, no killing of innocent bystanders, always respect the secret identity, only anal on fridays, those sort of things. I then lay the focus on them being a couple, with real couple issues, like lying, breaking promises, the villain becoming a true monster, but in the end they just work it out, and eventually get married. In the end they both get out of the biz because they're just getting too old for this shit.