Good Boys <3 Bad Girls

[redbrunja]

So, a question that I shamelessly stole from another lj-er during the fandom questions tennis match meme was about Good Girl/Sociopath versus Bad Girl/Good Boy versus Bad Girl/Bad Boy pairings.

However.

The flaw (to my mind) is that Bad Girl/Good Boy pairings are shamefully unrepresented *.

All I could think of for examples were Gail/Chis** (Rookie Blue); Katherine/Stefan (TVD); Cersei/Ned (Game of Thrones); Blair/Dan (Gossip Girl); and Cara/Richard (LotS).

Which is actually more than I thought I would find.

So. Flist. Talk to me about this vital issue.


*For that matter, so are Bad Boy/Bad Girl pairings.

**You could also argue that Gail/Dov also works fro the Good Boy/Bad Girl pairing, but I feel like they way their personalities bounce off each other and the shape of their arc disqualifies them. However, I am happy to have someone argue with me about that.

Comments

[ancarett]

Starbuck (Kara Thrace) / Apollo (Lee Adama) in BSG is another bad girl/good boy pairing that's a favourite of mine.

[redbrunja.livejournal.com]

Trufax.

[crackers4jenn.livejournal.com]

What about Kara/Lee from Battlestar Galactica? That counts as Bad Girl/Good Guy. And Wesley/Lilah from Angel, to some extent. Quinn/Finn from Glee. Maybe Britta/Troy from Community. Also, to completely shame myself: Sam/Freddie from iCarly.

[jade-sabre-301.livejournal.com]

SEDDIE. I am still crossing my fingers that they are not done for good. I hear the episode where they broke up is complete bs, so I haven't gotten around to watching it.

[redbrunja.livejournal.com]

This is a shame-free zone.

Kara/Lee is a great example. As is Wesley/Lilah. I don't feel Britta/Troy quite works, but Quinn/Finn does nicely.

[callmeonetrack.livejournal.com]

My OTP Starbuck/Apollo has bad girl/good boy overtones with her being the rebel and him being the strait-laced guy on the surface, but they're actually both rebellious and flawed and good-hearted when you delve a little. ;)

I actually like that kind of match-up a lot and would also say that Keith/Watts from Some Kind of Wonderful fits this. Also maybe Cordelia/Xander (Buffy). Hmm it is tough to come up with too many of these.

[callmeonetrack.livejournal.com]

Hehe, I see other folks beat me to the punch. Great minds. ;) Also, wasn't going to offer non-canonical pairings but I see you have Cersei/Ned above, so Johanna/Gale from THG?

[redbrunja.livejournal.com]

Cordelia/Xander is a great example.

My OTP Starbuck/Apollo has bad girl/good boy overtones with her being the rebel and him being the strait-laced guy on the surface, but they're actually both rebellious and flawed and good-hearted when you delve a little. ;)

Starbuck/Apollo is a GREAT example. I especially like (and this is likely due to old!Starbuck being male) that Kara is 'bad' in classic 'bad boy' ways; lack of respect for authority, aggressive, a drinker, and relatively promiscuous.

[nenena.livejournal.com]

Batman/Catwoman. Always and forever my favorite good boy/bad girl pairing.

Also Xander/Anya from Buffy the Vampire Slayer.

I think it's pretty clear why bad girl/good boy pairings are much rarer than the reverse, however: Because although "bad girls" can be an alluring fantasy for a male audience, in the end they always get punished for their "badness" (which is often intertwined with them being punished for exerting any sort of sexuality). And any fundamentally good male hero must be rewarded for his goodness with a pure-hearted love interest in the end. Meanwhile, both male and female audiences are consistently fed the idea that a bad boy can be changed by the Love of a Good Woman, so there you go.

Or, in other words: Because patriarchy.

If you're open to taking examples from anime, however, you've suddenly got approximately three billion examples of good boy/bad girl pairings, because The Love of a Good Man breaking down a tsundere girl's bad side and bringing out her softer, gentler, more submissive feminine side is an incredibly popular trope. But in the end it's every bit as sexist as the trope about how any fundamentally good guy will be rewarded with the love of the "good girl" in the end.

[surreallis.livejournal.com]

Yessss! I was going to comment in a like way. That it's interesting (and by 'interesting', I mean 'aggravating') how bad boys are often seen as misunderstood or hiding a heart of gold, while bad girls are usually just bad. And sexual promiscuity or aggression is used as, I'd say, the most prominent or number one symptom that the woman is EVIL.

Which (to redirect back to redbrunja) is one of the reasons I really like Gail in Rookie Blue. Because she's so much more complicated than that. She's often rough and curt, and it's seen as annoying, but even if the other characters joke about her being evil, they don't mean it. They still see her as family, and we see plenty of emotion from her.

She and Chris make a neat, complimentary couple. And I think if they go ahead with the hinted Luke/Gail, that will be neat as well, because for all Luke did to be an a-hole this past season, he's basically a good boy at heart.

[nenena.livejournal.com]

Oh wait shit I can't believe I forgot: Scott Summers/Emma Frost.

Because Batman/Catwoman apparently wasn't a geeky enough example from me.

[redbrunja.livejournal.com]

DO NOT EVEN GET ME STARTED ON HOW X-MEN: FIRST CLASS RUINED EMMA FROST.

AND I DIDN'T EVEN READ THE COMICS.

Sorry about that. But I think Scot/Emma is a fantastic example.

[irony-rocks.livejournal.com]

Kyle XY - Jessi/Kyle. (What? Don't judge me for liking that show, okay? It was oddly addictive!)

Angel - Lilah/Wesley.

Buffy - Anya/Xander, kinda, sorta?

Pretender - Ms. Parker/Jarod.

[redbrunja.livejournal.com]

Kyle XY - Jessi/Kyle. (What? Don't judge me for liking that show, okay? It was oddly addictive!)

I have no room to judge, trust me.


Angel - Lilah/Wesley.

Excellent choice.

Pretender - Ms. Parker/Jarod.

I have heard many good things about this dynamic.

[mistaria.livejournal.com]

I think Batman/Catwoman is probably the good boy/bad girl pairing. It's been going on for 70+ years, after all. :p It's my first ever OTP too.

I think bad boy characters are usually looked at as only needing the love of a good woman to settle down and stay in a stable relationship whereas a bad girl is looked at as the character who isn't going to change and who isn't going to stick around in any sort of a stable relationship for very long. I mean, that's what they consistently do with Catwoman; she's never going to be someone who sticks around in a stable relationship for long. Although honestly I get it in the case of comic books because some of these characters (like Batman/Catwoman) have been around for so long that they have to do different things and explore different relationships with characters otherwise people would get sick of it. ::shrugs::

[redbrunja.livejournal.com]

First of all, Catwoman/Batman FOR THE WIN.

I think bad boy characters are usually looked at as only needing the love of
a good woman to settle down and stay in a stable relationship whereas a bad girl is looked at as the character who isn't going to change and who isn't going to stick around in any sort of a stable relationship for very long.

You have a great point about the different expectations for bad girls versus bad boys, in regards to what they need and kind of what their damage is. And I absolutely think it's harder to do a romance over decades in an ongoing form than it is in a limited timeline.

[qualapec.livejournal.com]

Ooh! I was glad to see the mention of Cara/Richard.

There are a couple in the Dresden Files, I'm pretty sure. However, I'm not sure any of them are super popular in-fandom, except maybe Molly/Ramirez qualifies.

Leon S. Kennedy and Ada Wong from Resident Evil will always be my favorite.

I know you aren't familiar with the series but...just watch this scene and tell me that is not massive foe-yay:

http://www.youtube.com/watch?v=b2x5GcOqsGg

[redbrunja.livejournal.com]

Ooh! I was glad to see the mention of Cara/Richard.

Yeah, I don't really ship it (all about Kahlan/Richard, in that fandom) but it is a GREAT example of Bad Girl/Good Boy... as is Leo/Cara.

I know you aren't familiar with the series but...just watch this scene and tell me that is not massive foe-yay:

http://www.youtube.com/watch?v=b2x5GcOqsGg

Oh, no, that is MASSIVELY Foe-Yay.

[norgbelulah.livejournal.com]

From my phone so this is brief.

Kalinda/cary. <3

Obv. She's not completely bad. But he fr real can't take her home to mother. :P

[redbrunja.livejournal.com]

Oh, hells no. Could you imagine taking Kalinda to meet the parents? That is a total recipe for disaster. DISASTER.

[ever-neutral.livejournal.com]

Amen.

Though, I'm surprised you'd include Blair/Dan as a Bad Girl/Good Boy. I often see Blair being described as a "Good Girl" in her relationship with Chuck ("Bad Boy"). Eh.

[redbrunja.livejournal.com]

Yeah, Blair is definitely the Good Girl in Chuck/Blair (or at least she is now, instead of them being sneaky, devious Upper-East-Siders together, a la Season 1). However, with Dan, I get a more Good Guy/Bad (or slightly naughty?) Girl vibe.

[hungrytiger11.livejournal.com]

....I think that one could argue that Katniss/Peeta could be viewed as Bad Girl/Good Boy. She regularly breaks the law; he's considered a "nice boy." She uses his affects to win the Game. Sure, she feels guilty and confused by her own feelings but they were definitely not, shall we say, clear to her at that time. Peeta repeatedly is shown as self sacrificing and this "good" person who should be a natrual leader- at least to Katniss mind. She feels she's lying to people all the time.

But it doesn't come off as Bad Girl/Good Boy because we are viewing the story from Katniss. We are meant to symphasize with her. And, of course, we are limited to her thoughts on the matter. A more neurtral party or, heck, most other characters besides her or Peeta might view things differently.

And, of course, a lot of the gender roles are subverted here, so its nice to see these dynamics don't matter as much...

[redbrunja.livejournal.com]

I actually don't think Katniss/Peeta work as a good guy/bad girl pairing. There are a lot of narrative gender reversals (which I could rave about forever), but Katniss is pretty firmly in the role of family protector and provider, and she's breaking the laws of an oppressive regime. I think the only person who views her as not good enough for Peeta is Haymitch, and I firmly believe that is comment to that effect is more indicative of his own self-loathing and the way both he views Katniss and similar to himself.

[whisperingwasp.livejournal.com]

The flaw (to my mind) is that Bad Girl/Good Boy pairings are shamefully unrepresented

YES. YES. I love this trope but I can only remember one show that did it when I was a child and even it's name has escaped my mind.

And Blair/Dan. ♥ I swear, they're one of the reasons I still keep watching the show.

[redbrunja.livejournal.com]

I know someone who both absolutely loves the Dan/Blair and also hates it because if the D/B would disappear, she could quit the show.

[12-12-12.livejournal.com]

Oooh, Bad Girl/Good Boy pairings. Yes, they're rare, for really obvious reasons having to do with writers pandering to fans rather than simply writing stories IMO. I think "bad girls" present the allure of giving into their own darker impulses for the audience. Whereas "bad boys" present the prospect of reforming the boy/changing him for the better as a demonstration of your ~power over him, the power of his lurve for you (and therefore, how ~*~special~*~ you are.)

So redemption--and the relationship that comes along with that--is not the point of a Bad Girl. They're often killed off instead as the culmination of a story where Good Triumphs. And even if they don't get killed off, they usually aren't "rewarded" with love because fandom thinks the bitch doesn't deserve it. Even in ships, the Bad Girl is often not "the one" for the guy--in many cases she's held up as inferior to some other girl who's deemed "gooder" in some way. RME. The number of people I've seen saying that Dan "deserves better than Blair," I CANNOT EVEN. It makes me so angry. Because how many pairings have you seen where the guy blatantly does not deserve the girl? And fandom loves those pairings all the more b/c they're all swoony over how her love will ~saaave him and she's the ~only one~ who can ~touch ~his ~heart. (Besides which I disagree that Blair is "undeserving" of Dan in any way, so anyone who thinks that can go jump off a cliff for all I care.)

But as ever_neutral points out, I don't think Blair is a "bad girl" in the same way as a "bad boy" is bad. Unlike Faith, who was really unusual because she was "bad" in almost exactly the same way that "bad boys" are "bad": sexually promiscuous, criminal/antisocial tendencies, abusive childhood, physically violent, commitment-phobic and with a gazillion trust issues, deliberately hurting/testing those who try to help her b/c she doesn't believe they will truly stick by her. Blair isn't like that--she's a romantic at heart, she's a relationship girl, she comes to people's rescue, she's loyal, and she treats guys well when she's dating them...I mean, forget Bad Girl ships, I think it's hard enough to even create a Bad Girl character in the same way as a Bad Boy and have the audience swallow it: fandom is THAT biased (it only worked with Faith because she was so well-written and Eliza Dushku had a ridiculous amount of raw sex appeal.)

P.S. I love your thoughts above about how women in fiction are often punished for having agendas and desires of their own (SO TRUE), and that this might be why there are so few female "Honorable Enemy" characters. I hadn't considered that before.

P.P.S. I'm bothered by the use of sexual aggression and/or promiscuity as an indicator of "badness" in girls to begin with. WTF.

[redbrunja.livejournal.com]

I think "bad girls" present the allure of giving into their own darker impulses for the audience. Whereas "bad boys" present the prospect of reforming the boy/changing him for the better as a demonstration of your ~power over him, the power of his lurve for you (and therefore, how ~*~special~*~ you are.)

I think this is exactly it, and besides being straight up sexist, ties into writers not realizing that SOME members of the audience would connect strongly to the 'bad girl redemption arc'.

It makes me so angry. Because how many pairings have you seen where the guy blatantly does not deserve the girl? And fandom loves those pairings all the more b/c they're all swoony over how her love will ~saaave him and she's the ~only one~ who can ~touch ~his ~heart.

Right? Right?

But as [info]ever_neutral points out, I don't think Blair is a "bad girl" in the same way as a "bad boy" is bad. Unlike Faith, who was really unusual because she was "bad" in almost exactly the same way that "bad boys" are "bad": sexually promiscuous, criminal/antisocial tendencies, abusive childhood, physically violent, commitment-phobic and with a gazillion trust issues, deliberately hurting/testing those who try to help her b/c she doesn't believe they will truly stick by her.

One of the gajillion reasons I love Faith so much... and yes, when writers start writing bad girls, they go for an entirely different set of tropes and behaviors than they do for bad girls.

Hmmm. Now I want to ponder this in regards to Nikita, because I feel like there is more to say about that show and how it sets up its heroines...

P.S. I love your thoughts above about how women in fiction are often punished for having agendas and desires of their own (SO TRUE), and that this might be why there are so few female "Honorable Enemy" characters. I hadn't considered that before.

I think that's one element in why. Also, a lot of times female villains are motivated by love, instead of money or (and this is the classic motivation that leads to honorable enemies) loyalty to something larger - a country, an organization, etc.

P.P.S. I'm bothered by the use of sexual aggression and/or promiscuity as an indicator of "badness" in girls to begin with. WTF.

SO MUCH HATE FOR THIS. SO MUCH.

[nenena.livejournal.com]

Okay, so, having slept on this, here are some of my favorite examples of bad girl/good boy pairings from anime that aren't completely sexist rehashings of the tsundere or yandere tropes:

Category 1: Unresolved love triangles
In these stories the pure-hearted male protagonist falls in love with both a Very Bad Girl and a Very Good Girl and ultimately never does choose between them, because TPTB are savvy enough to know that if they ever actually resolve the love triangle they would create an apocalyptic shipwar among the fans. So.

Tenchi/Ryoko from the Tenchi Muyo! franchise
Kyosuke/Madoka, Orange Road
Shinji/Asuka, Evangelion (which was nixed in the film reboot, but was there in the original series)
Naota/Haruko, FLCL
Keiichi/Rena or Keiichi/Mion, Higurashi no Naku Koro Ni

Category 2: Endgame ships
These are much stronger examples of "the pure-hearted hero breaks down the Bad Girl's 'badness' and brings out her sweet submissive side," so they're a little more blargh, but I think that these examples are well-developed enough to be interesting despite falling into the trope. And a few of them even manage to subvert the trope.

Gourry/Lina, the Slayers
Raki/Clare, Claymore (Clare isn't "bad" but she does have an evil/monster side)
Madarame/Saki, Genshiken (avoids the trope completely but mostly because they don't end up together in the end)
Kyon/Haruhi, The Melancholy of Suzumiya Haruhi
Dan/Miya-Miya, Bamboo Blade (LOVE this pairing)
Roger/Angel, The Big O (although they were based on Batman and Catwoman)
Mytho/Rune, Princess Tutu (subverts the trope entirely)
Ray/Scarlett, Steamboy
Araragi/Hitagi, Bakemonogatari
Anemone/Dominic, Eureka 7
Ryuji/Taiga, Toradora!
Battler/Beatrice, Umineko no Naku Koro Ni (definitely an UR-example of the trope)
Nagasumi/Sun, Seto no Hanayome
Makoto/Ifurita, El Hazard


...and I tried to avoid any anime that was based on a dating sim, since you'll inevitably get a ton of "bad girl" characters to pair the male protagonist with in those types of series.

[redbrunja.livejournal.com]

Shinji/Askua was such an interesting pairing. And I have such affection for Rue/Mytho.

Thanks for the examples!

[borg-princess.livejournal.com]

Hmm, I had a tough time trying to think up one...and then I remembered my new fave show! From Revenge, Emily and dude from Make It Or Break It, whose name I cannot recall right now. She's so terrible and hellbent on destroying his family and it is glorious, lol.

It's early days yet, but bad boy/bad girl could be Faye and Jake from The Secret Circle, if the writers explore that. Though it's more likely he's gonna be ANOTHER love interest for Cassie.

If you relax your definition of 'bad', then there's Ce'Nedra or whatever her name is from the Belgariad books by David Eddings. Ye gods, I hated her guts- so spoiled, a terrible brat, just absolutely selfish, ugh. Still, there's a lot of 'bad boys' who are basically the same but idolized for those traits, so I'll keep her in.

Oh, Fringe! In season 3, Fauxlivia and Peter.

Aaand that's it for now.

PS. Since you included Cersei/Ned, which has to be fandom (unless that was explored in the books but not the show), I'll add Morgana/Merlin to the list. I ship it not at all, ugh, but it's apparently popular.

PPS. Ruth Wilson's character from Luther, Alice Morgan! And Luther's, IDK, I think he started off good and ended up being a psycho as well or something, so I hear, which is interesting. Speaking of psychopaths, there's Dexter/Lilah... *ponders* Okay, I think I'm done.

[redbrunja.livejournal.com]

Oh, I definitely think Emily applies. Damn, I love a girl on a rampage of revenge.

PPS. Ruth Wilson's character from Luther, Alice Morgan! And Luther's, IDK, I think he started off good and ended up being a psycho as well or something, so I hear, which is interesting. Speaking of psychopaths, there's Dexter/Lilah... *ponders* Okay, I think I'm done.

Alice/Luther is definitely a good guy/bad girl pairing, although I could see it ending up bad girl/bad guy.

And ugh, Lilah/Dexter. I love the actress who played Lilah but I hated the character SO DAMN MUCH.

[yahtzee63.livejournal.com]

You could maybe argue that Jack Bristow/Irina Derevko from "Alias" fit this trope; Jack is not really a "good boy" -- he's ruthless -- but he's allied with the white hats, and no matter how bad he might be, Irina is definitely a whoooooole lot badder.

To some extent, I think Amanda/Jack on "Revenge" is shaping up to be a bad girl/good boy romance to remember. Amanda is fundamentally after justice, but her methods are as low-down as any villain's you've ever seen.

Now that I think about it, soap operas used to have real fun with this trope all the time. Erica Kane was loved by any number of good boys -- Mike, Jeremy, Nick, Tom -- and used them all up in turn. And while never ceasing to be a "bad girl," switched from a show villain to the number-one heroine. God, I miss her.

[redbrunja.livejournal.com]

Oh, I would definitely count Irina/Jack as a good guy/bad girl ship, especially in their backstory, when she was was spying on him.

[ivanolix.livejournal.com]

Blair/Dan and Cara/Richard <3 <3 <3

I'm a big fan of Bad Girl/Good Boy pairings, and you're right, there are woefully few around.

My examples:

Most het Cara ships AND het Richard ships (LotS)
Most het Kara ships AND het Sam Anders ships (BSG)
Ellen/Saul (BSG)
Jolinar/Martouf (Stargate SG-1)
Vala/Daniel (Stargate SG-1)
Veronica/Ted (Better Off Ted)

I feel like April/Andy on Parks and Recreation almost qualifies...but while April would be a Bad Girl on any other show, she isn't on that one. Which is a good thing.

[redbrunja.livejournal.com]

Yeah, Parks & Rec doesn't really have bad characters. And yeah, I love how April's snark is just part of who she is and traits that would make her a terrible employee are why she's valued by Ron.

Most het Cara ships AND het Richard ships (LotS)

Ha, ha, oh Richard, and your delicious abs.

[tigerpetals.livejournal.com]

Revenge seems to be setting up a bad girl/good boy pairing with Emily/Amanda and Jack, or with Daniel. She's had a horrible life and is calculatingly destroying the people who made it that way. Jack is the nice poor guy she used to be childhood friends with, and she lets down her guard a bit around him. Daniel is the son of her enemies, and he's kind of a sweet reformed guy with a bad boy backstory.

[redbrunja.livejournal.com]

You're right, both of those pairings are good boy/bad girl. Oh, Amanda.

[iluvtheukoffice.livejournal.com]

My first thought when I saw the thread subject was "Does Cary/Kalinda count as good boy/bad girl?" (She is definitely the darker/edgier one; he's not pure as snow, but there's a naivete and a decency to him that is in contrast to her deep-rooted cynicism.) Then I peeked in here and saw that [b]norgbelulah[/b] mentioned them, which makes sense because her C/K fic is the reason I found my way over here.

Another bad girl/good guy ship I loved was Trixie/Sol from "Deadwood". I think most viewers responded more to Trixie/Al (which I openly admit were awesome as well), but I found all aspects of that triangle fascinating. I wish that the show had gone on for a lot of reasons, but one of my biggest disappointments in it ending where it did was the loss of Trixie/Sol when their story was getting really interesting. The moral choices they made in the last few episodes of the series promised to lead down some very dark and twisted paths if the show had continued. David Milch hinted as much, and I know John Hawkes and Paula Malcomson would have rocked that material.

In more recent pairings, Mary/Matthew of "Downton Abbey" seem to fit the bad girl/good boy mold (at least for the early 20th century setting). I do appreciate that they established fairly early on she does have a heart and the capacity to care for others (even if it's well hidden). I am trying to stay spoiler-free for S2, so I'm not sure how the continuation of their story is shaping up these days.

I have a long history of watching soaps and much of my shipping experience is tied to that world. I think I've shipped all possible good/bad soap couple permutations, but it's definitely accurate that bad boy/good girl are the most common (or at least most popular). I think that a big part of the allure, for me, is the contrast. When characters start out on the same plane (good/good or bad/bad), I don't see as much room for push/pull and character change/growth. (And, admittedly, that may not be because there isn't,/i> as much potential, but because writers have been locked into the same tropes for decades at the expense of any true creativity.) Reva/Josh (GL), Blake/Ross (GL), and Carly/Jack (ATWT) are a few of the strongest examples of bad girl/good boy soap pairings I can think of, or at least the longest lasting.

[iluvtheukoffice.livejournal.com]

Uggh. Saw the damn missing italics tag as I clicked "post comment". And now I see the failed bolding. I am so bad at html I just shouldn't bother. *hangs head in shame*

[despairinbeauty.livejournal.com]

Very good point. This. THIS is another thing that I am not liking in the system. Why is it that the guys who are sociopaths can be "reformed", but the girls who are will never be and are often punished? Seriously...

And, not to mention, so many fanfic authors throw themselves into the idea of reforming a male sociopath for a good girl that it scares me. X.X It's just that serial killers and psychos really are NOT that cool to be around, whether in believable fiction or in reality, and I will admit that I don't generally like good girl/bad boy pairings for the most part (exception is Izaya/Rio, but that's because it is purposely dark and the guy never "reforms"). ^^; Bad girl/good boy, though, are actually slightly more likely to make it on my list in ways.

So, yeah, the idea of all "bad" girls being not reformable is damnedly flawed, in ways. If the bad boys can be "reformed" (and I personally tend to dislike bad boys/psychopaths/sociopaths even if they are just characters ^^;), then the girl 'psychos' are even more likely to grow and change, mainly likely because women sociopaths are...less likely to be seen as cool for what they do, I guess.

But, agreed so much on the sexuality being seen as the bad thing done by the female sociopaths in here. X.X If they are seen as bad because of it, why aren't the bad guys also seen that way as well? The only reason I can think of that actually would make me dislike a female character would have to do with her being incapable (even as an antagonist, if she's strong and capable in ways, I would like her).

[despairinbeauty.livejournal.com]

As for pairings...

Bad guy/good girl: Izaya/Rio (Durarara!!). The only one I know of that I find interesting, mainly because it is dark and twisted and the guy is not reformable.

Good guy/bad girl: Kouga/Kagerou (Basilisk). Said bad girl (as beautiful as she was) never managed to be with him because she was born to be inherently poisonous to anyone she sleeps with, and because the guy was attracted more to the good girl (Oboro).

Darn. I wish I knew more...but, Shinji/Asuka (Neon Genesis Evangelion) is also kind of one for me. Though, I do find platonic Shinji/Rei okay (platonic only, though. XD Since Rei is not really what I consider relationship material at this point)