*Names have been changed to protect the fictional.
Nyah wants to know: I don't want Vincent to come across as a misogynistic sadist. He's not violent by nature but he feels vindication in the idea that Jay should suffer the same fate as Vincent (losing his wife and daughter). He's regretful that the women have to suffer, but how do I portray this sympathy to the reader? What characteristics/behavioral traits could I give him to make the reader more sympathetic of him?
These are great questions, and some that I think a lot of my readers will be interested in. What makes someone else sympathetic in the eyes of others?
You have Vincent going through a very traumatic event of having to be made witness to the murdering of his wife and child. I can think of no circumstances that something like this would not change him. I believe you said he was imprisoned directly afterward, which would also effect his grieving process (delaying it simply to survive, etc).
Witnessing the murder of someone you love could enrage a person, depress them, numb them--you've really got a lot of leeway with how it will affect him. If his main urge is revenge, and it's got to lay dormant for 10 years or so, that bitterness and sense of unfulfilled justice would likely eat away at him. So while he might not be an inherently violent person, his personality would have changed.
I don't think that Vincent will have a strong attachment to Jay's new love interest. It's the general unfairness of Jay being relatively happy that fuels your antagonist, not specifics, such as Kathy's job with the government being reminiscent of Vincent's experience with governmental agencies. So I'd say stick with the internal motivation of his need for revenge rather than make the leap to Vincent also being externally motivated by some attempt to "get back" at the government for what happened to his wife.
As far as him being sympathetic to the necessary evil he must put Kathy and Jay's daughter through, there are a few things you could do to make him more sympathetic to the reader and less of a monster.
1) Distance Vincent from the means to his end. In other words, have Vincent focus on the feeling of relief and justice that he believes will come once Kathy and the daughter are dead, not so much on the process of getting them there.
2) Show Vincent giving Kathy and the daughter some form of kindness, no matter how small. perhaps the little girl reminds him of his own, so therefore he allows her to keep her stuffed Dora doll with her. Or maybe he provides them with a cushion instead of making them sit on a hard cement floor. It won't take much to clue the reader in that Vincent might not have fully realized the process he'd have to go through (of killing these females) to make his version of justice a reality.
3) Make Vincent obviously mentally unbalanced as the scenes with the women progress. I'm reminded of the scenes from Silence of the Lambs when Wild Bill has the senator's daughter down in that hole. He's sending her just a little food and lotion (obviously for the really gnarly reason of making her skin softer and more malleable once it's removed) and he keeps referring to her as "it." "It puts the lotion in the basket." No one alive would listen to that and think Wild Bill is anything less than crazy. Given his background and what the reader comes to learn about him (i.e., what might have made him crazy), it's hard not to feel a little something for the guy.
4) Give him some poignant flashbacks. (These could be real tear-jerkers, too). If Vincent's mind is unable to stay in the present as he's abducting Kathy and the girl, then it would give him a vulnerability in the reader's eyes...that he's still so grief-stricken that his mind keeps pulling him back to the past. Another way to possibly do this would be to have Vincent steeped in old video footage (or whatever the equivalent would be in your futuristic world) of his former life, when his wife and daughter were still alive. Maye he constantly pulls out a photo of his family to stare at it, and imagine what life could be like for him if they had lived.
You were wondering if the fact that he is sympathetic to their plight would be a precursor for some other type of psychological disorder, and I feel it appropriate to mention that there is a syndrome named for this very phenomenon: Lima syndrome. Now, this is not in the Diagnostic and Statistical Manual for Mental Disorders, but Lima syndrome is considered the reverse of Stockholm syndrome. Perhaps if you research it in Google, you might find something usual.
Another question you asked was at what point does grief morph into bitterness and then bitterness into vindictiveness? And at what point does a desire for justice mutate into a desire for revenge? (That last one is a great blurb question for the back cover copy of the book!)
As you can tell from my posts on grief and my more concise Writer's Guide for Grief, there is no correct answer for how it progresses. I believe in Vincent's case, his grief would have ample time to turn to bitterness in that 10 year period. 10 years and then seeing his perceived enemy having made a life for himself with a wife and child very much alive, made even more damning because Jay's child is a daughter as well.
I believe the seed for vindictiveness would be planted early, though. Perhaps while his wife was being murdered--maybe that vindictive thought that he'd kill Jay or Jays loved ones kept him from going crazy as he watched the murders. (Think of the comic strip characters with raised fists who yell, "I'll get you for this!!") It would have fueled him through those 10 years, and he would have stoked the fire of his anger/wrath that entire time.
That's all I've got, Nyah. I hope that this helps. Feel free to drop me additional questions in the comment section. Good luck...sounds like a fascinating book. :)
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