A complicated anti-heroine?

I have a power-seeking guile heroine from tumultuous circumstances who always gets in over her head, and a reluctant hero who keeps saving her. It's a pattern. She (more or less) stays the same, it's just her schemes that get bigger.

She's a con-artist with a broken moral compass, but she's also suppose to be intuitive when it comes to reading other people, the idea is she is a bit empathic (not supernaturally, just plot-wise) but also a bit of a sociopath who mirrors the morals and goals of those around her. She pursues powerful people, good or bad, but eventually screws them over even when that wasn't her intent. She is like Aesop's scorpion, she can't help her nature. Around the point where things start going her way, a machination from earlier comes back to bite her, and she grabs the money and runs while all hell breaks loose.

She is a chameleon who presents herself as whatever others want, including the hero's desire that she can be redeemed. Her "bad" nature is first discovered only in escalating stages of the plot, while the hero is still in denial and there is a chance they will get together. She goes from being an innocent "victim of circumstances" to a sudden pile-up of anti-social reveals that got her there in the first place.

However, I want her to remain sympathetic: a complicated heroine. In later stories she will repeat the pattern but it is no longer a surprise to the reader (or the hero) so we watch her dig herself a deeper hole, then cover-up and self-sabotage. It's clear that she gets herself into situations – she's an opportunist who drives the plot forward.

My problem with her character:

My snag with her character is that she doesn't think she is the problem, in her mind she is just tap dancing around powerful and dangerous people. She doesn't debate morals, at least not in a way that shows. Her rare moments are when she does the right thing for the right reasons because in a part of her mind she's always nurturing a smash-and-grab strategy and a quick escape.

In contrast, the hero has self-doubts and questions his own morals. The reader has a better understanding of his internal conflict because he reacts to his mistakes, and has periods of mania and depression. He goes through a lot of soul-searching, understanding his need to save her and also learning he can't change her.

How do I show this heroine is sensitive/intuitive about other people, uncovering their buried vulnerabilities and secret desires, and yet unaware that her own schemes are her downfall? She is sort of an iconic femme fatale who keeps climbing to the top. But why would she keep running to danger, rather than just finding a rich guy she could manipulate and live comfortably? I feel like I am relying on "it's just her nature" to keep them in this pattern forever, but that implies she is a psychopath or maybe a convenient moron.

How does the heroine keep getting into trouble without realizing that she is the source of the trouble?

  • 5
    Why do you think your heroine should seek a commitment with "a rich guy"? She may be repelled to the very idea of "belonging" to someone (even if that someone is being manipulated by her), and think that "tap dancing" is the right way to get ahead in life.
    – Alexander
    Sep 28, 2018 at 17:17
  • @Alexander, I understand her attraction to power (whomever is in power at that moment), but I'm not sure how to convey that to the reader without making her seem like a villain, or at least very shallow and fickle person. A hero that is attracted to a beautiful damsel in distress is different to a gold-digger who climbs a social ladder presenting herself as something she's not. I think you're also maybe being cavalier about how women are judged by their sexual choices…. I didn't say she should marry a rich guy, but how does this not happen naturally…? Why always go for a "bigger" prize?
    – wetcircuit
    Sep 28, 2018 at 17:27
  • 1
    Do you think of her more as a con artist, or just golddigger? The former would get more sympathy from the reader. Why she doesn't marry (or otherwise commit) - some people are fiercely independent, she can be one of them.
    – Alexander
    Sep 28, 2018 at 17:37
  • 1
    If you have not watched the early 1990s TV Series Gargoyles (Disney) I highly recommend watching the Character of Demona to get some ideas of this character... she's less anti-hero and more pure villain, but she shares a fault. I highly recomend you watch the series premier (5 part episode), "The Awakening" and the season 2 four part episode "City of Stone" which essentially is in part "The Awakening" from Demona's point of view. " Vows" might be another good idea where we see how she got the idea. It's probably not helpful for a less fantasy setting... but it's got some cool concepts.
    – hszmv
    Sep 28, 2018 at 19:06
  • 1
    Reminds me of Inanna too much. Gets in trouble, check (Descent to the Underworld); femme fatale, check (Descent to the Underworld); strives for power, check (Descent to the Underworld, Inanna and Enki, Inanna Takes Command of Heaven); sympathetic, check (she is sometimes called sister-in-law of people). But regarding last point it might be just me, because in any story I myself would be an anti-hero (driven by unconventional benevolence, though).
    – rus9384
    Oct 3, 2018 at 6:52

3 Answers 3


I would have her planning one huge con that could set her up for life, but she needs experience. These earlier cons might be stepping stones, which occasionally heat up and she always manages to escape. She is looking for that whale that might even be talked about but could certainly allow her to leave the life should she choose. Until then, it is keep your eye on the big picture and move toward your future.

Maybe she thinks that the hero is just another mark who has a convenient habit of being her white knight. She resents the damsel in distress idea because she is certain her own wits are more than enough to get her out of the trouble she encountered.

She might be unaware of his efforts and believe it is just luck and she has the catlike ability of always landing on her feet.

She doesn’t think that what she is doing is wrong, it is just another way to make a living in a harsh world. She believes that violence is wrong, but if people are foolish enough to give her money then so be it.

The ability to read other people is essential to her success as she must know what the other person wants and needs in order to create a false truth which the listener will believe. It must fit the circumstances she observes. She can be brilliant at it and still not see herself clearly.

She avoids introspection as a waste of time and focuses on those around her. She might begin to wonder at the amazing run of luck she’s had and come to believe that the marks are just an unlucky lot, not noticing the connection.

The how? I would have her observe her marks, studying them before ever they realize she is there. She will have all of the answers to their objections before ever they think of objecting. She will be smooth.

The reader and the hero will see that she causes all of the trouble. She does not have to notice that for quite a while. Just have her focus on other things and show other aspects of her so we understand why the hero cares so much about this bad seed.

Was she kind to a neighbor of his? Kind to him? Probably for her own reasons, but even so, some acts of kindness can be genuine. She is severely damaged, but not utterly destroyed.

Can she be redeemed? Not unless she wakes up to her reality and chooses to change. Not likely. Show why the hero thought that she was worth the trouble, worth his efforts. There must be some glimmer of good that he thinks he sees though he might be mistaken.

  • 3
    Wow. It's like you know this woman. Great insight, she is absolutely against violence, but fine with stealing. Other assumptions are correct too…. I will go back and make sure there is a genuine connection (however brief) between them, not just him feeling sympathy or being fooled.
    – wetcircuit
    Sep 28, 2018 at 17:47

I think the two questions you'll need to answer for this woman are where did she come from? and where is she going? What in her back story made her into the person she is? And what goal is she pursuing that makes it all seem (to her) like the ends justify the means?

Aside from that, she doesn't sound all that unrealistic to me. People can often be very self-sabotaging in real life, and it's possible to be clear-eyed about someone else, and blind about yourself. In fact, I'd venture it's more the rule than the exception.

Self-sabotage is often a result of feelings of worthlessness or guilt, a sense that one does not deserve better. Sometimes it can even be paradoxically self-preserving, a way to avoid a situation that is good in one way, but a trap in another. Conversely, it can stem from a fatalistic desire to ruin something before fate can ruin it first.


I think, that it could be of use, to see her as two personas in one body. (She may be or maybe not actually schizophrenic, she may be just more complicated person, than she looks at first glance - more about it later, now just for simplicity let me use two personas scheme for a moment.)

First persona, which anybody can see, is a "Blonde" (cause I am blonde/ I don't have to think/ I talk like a baby/ and never pay for drink ...) - naive, cheerfull, with "superpowers" of "Empathy", "Mirror" and "Living just Here and Now" with pure heart and empty head.

She meet a boy A and from first look she LOVES him. Like TOTALLY. From deep of her heart. She believe it, she acts on it. He is just the "more FUN boy" she ever met. She is everything A ever wanted, she knows him better that his own mom and fullfill all his wishes just to make him happy (well with some acting, she would not end in bed with him this night, but makes him trust, she would really like and that it is not too far away, anyway making herself just a 'little' hard to obtain makes her just more prized in his eyes and make any progress he made much more satisfying for him.. ) ... Does not take long, they go to pub and meet A's friends, where there is one older, more serious (with better job too), say B.

She is just STUNNED how B is WISE and so she loves him from first evening they met. She loves hit like TOTALLY, from deep of her heart. Yes, A is still her old friend and she likes the fun around him and such, but it is just old friend (while kiss here or smile there does not mean nothing between old friends, you know) and it is clear, that he feels the same way (why would not he, it is soo long ago, whet it was serious between them - well at least weeks, or days or hours - he surely understand, that it is long dead history now)

She is everything B ever wanted, she uderstand him better that his own mom and fullfill all his wishes just to make him happy ... (as in previous paragraph), until one day she attend bussiness weekend with his colegues and his boss C (and guesss, what happens at that moment) ...

The other persona is a "MasterMind", who have "superpowers" like "create long time plans", "knows WhoIsWho", "Secretly Smart" and "Convice Blonde to trust anything she says". While Blonde is managing all about body, MasterMind thinks about carreer, fame, power ... not necessary evil, just a little selfish, narcistic and lazy - and have "broken moral compass".

MasterMind had long ago discovered, that showing how is she smart and responsible just leeds to lot of work and hard scolding and long morall lessons, when she does something "not so good" or just slack on something - while using Blonde style as frontend - known for being "irresponsible dumbhead all the time" brings a lot less of work and also easier one and doing anything bad just bring "oh no, again ..." response, which is much less trouble for her. So MasterMind worked hard on making better Blonde.

Yes, MasterMind had seen, how Blondes everytime jumps to a situation, steels someone hard work, ruin everything and went out mainly unharmed, confused what happened and with some unfair profit. And also had seen, how Bloneds later fall hard for just being stupid, too greedy or just too old for being the right Blonde.

But MasterMind think, that with some better planning and thinking (which those empty-head Blondes was not able to do) it would be simple and efficient way for everything - fame, power, money, jewels ... just name it. And that she just deserve it, becase she is exceptional and granted to have it all.

So well working Blonde with her excelent mind == profit!!!

MasterMind just looks at TV, hear the news, gossips and such and it is easy for her to realise, that Richard the Rich have friend D, who have friend C, who is boss of B who drinks with A who is in simple reach of Blonde.

So at right time she whisper to Blonde "the A is such FUN, would not he just be perfect friend for you?" And Blonde loses head for A. Later Mastermind whispers "A is just fun, but see, how the B is WISE, is not B who you really want?" and it happens ...

Actually the heroine is probably just the MasterMind, and the "I am Blonde" trick just was played too long and too good, that it became her second nature and mainly overtake the body from her - not that she cares, as "being Blonde" is just routine as is eating, doing homework, or simple tedious work, washing, sleeping, breathing - something she do nearly uncociously and what goes on autopilot, while she is dreaming about big future and perfect con-plans. But the habit is so perfected, that it became her personality more, than she think or is able to see.

So why there is always problem biting her back when the big success is at reach? Well, the Blonde now manage Epathy and Mirror and the Blonde believe ewrything what she wish, so her reports to MasterMind are sometime precise (as what A wants from her, when they meet first time, what are his aspirations, dreams ...), sometimes just little off or biased ("A surely thinks just of me and he loves me from his whole heart too, he would probably forgive me anything") and sometimes just pure lies (without intent, but Blonde use Empathy and Mirror against MasterMind too - she cannot NOT switch it off - so MasterMind hears just what SHE wants to hear, if there is not evidence against it)("A is my old friend and understand, that our phase of love if just deep history. He is still friend and would help me anyway, I can feel it, just trust my Empathy" - yes, it fits MasterMinds plans perfectly, so the small details - like that Blonde had not seen A from yesterday, when she met B and walked with him out, so A is probably now unsure, what happened, and thinks, that Blonde is still over head in love with him and yesterday was just bad dream, or will explain somehow naturally, like, that B is Blondes uncle - just does not came to Mastermind, after all Blonde's Empathy is real thing, we know it.)

And when next week Blonde runs to A, kiss him with "Oh hi, glad to see you, you you well, I am in hurry now" and leaves him totally confused while catching C's car, get flowers from him, kiss him and drive with him away (C:" Who was that young man", Blonde: "Ah, just some old friend of mine, it is long time ago history, but tell me ...") A:"WTF has happened, she dates B's boss now? @$%@#$%!! *)"

*) Untranslateble gealic cursing from Asterix

And Blonde still believe (as she want to believe it and there is no direct evedence against it), that A is "just old friend, who loves here a little, even after such long time not seen". While A is all to eager to get revenge, rather than to get explanation now.

MisterMind still trust Blonde anyway - she would not lie to her, as they are just one flesh and body.

Blonde is finally Rick's the Rich LOVE FOR LIFE, alone with his keys in his mansion. Mastermind whispers "what would hurt just to opent the tresor and try that diamond necklage, it must be beutifull on us and Rick surely would not mind anyway" and Blonde think so and does so, but then there are some steps on stairs - must be Rick's right hand Man, who do not trust Blonde at all. "It is too late to cover everything, so make it look like roberry, just throw some papers aroud, get the jewel box and run over balcony - I see A's car there on street, hes old friend, he will help us to gety away with it and would not ask why"

Then inevitable came, perfect plan fails. And who could expect, that A is such low man, taht not even helped Blonde, but helped her enemies and told them everything he had seen and even more. He sooo much disapointed her and after pretendind for soo long time to be friend, or even love, then he pushed her down, who knows why? (Reader know, that it is just the next time A see Blonde ater the kiss described above, climbing in negligee from Ricks the Rich Masonry, followed by some uniforms screaming "Burglar, burglar!")


  • MasterMind still believes Blonde and vice versa.
  • it was just all the work of the sneaky A, that perfect plan failed, nobody else is to blame
  • also it was A's devil plan, that B, D, ... Rick now hates Blonde, why is A is so evil?
  • Knight on white horse saved the day after all, as expected from old friend after all, he did it so many times, that one would think, he loves me or what, if he would not be just old friend of mine, who does it everytime. I would even kiss him, but he again start with his long boring moralisations, that I did not get attention to even hear
  • but now we know old good friend C, who single did not turn back on us, so we can came with much better plan, and he have sooo coool car and good taste in flowers ...

and some calculation to the end:

  • 99% of time everything went around the plan - MasterMind nearly won (if that A would not betray us who know why), just last 1 % time she was miscalculating
  • 98% of time Blonde had fun and a lot of friends, just 2% to perfection - 1% as per As betray in the end, 1% per Knight long moralisation, but he is still our friend after all

yes, depending on which angle of view you take, the heroine was just only 1%-2% of time in trouble at all :)

(Well readers may think something else, but who they are? Can any character in the book eve see their faces?)

(Also apologies, english is non my native, second nor third lang ... lot of typos and such)

  • I really like such stories:) If you fininish it, can I read it?
    – gilhad
    Sep 29, 2018 at 21:34
  • brilliant nuts-and-bolts breakdown of how she self-sabotages but is still convinced everything is working as planned. I love how Blonde and Mastermind flatter and agree with each other (feedback loop), also how Blonde can convince Mastermind everything will be fine – more important, Mastermind has a longterm reason to distrust others because they always change "for no reason". It even seems logical from that perspective.
    – wetcircuit
    Sep 30, 2018 at 15:16

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