Yes, even the worst Jew still has a beautiful shining soul underneath all the muck. So the potential you may sense is definitely there.
But practically speaking, some people really are trying to hurt others, maybe even enjoy hurting or embarrassing others, really don't care about anyone except themselves, and really aren't motivated to change no matter how much their behavior is harming themselves or others.
Some people really aren't interested in even starting the work it takes to make even a smidgen of teshuvah, no matter how much support they receive from a friend or counselor or rebbetzin.
So in order to find that meritorious quality or deed, you may need to sideswipe a lot of muck and detour into a completely different area of their personality in order to find the merit.
I think this also explains why, many times, the very person you spend hours listening to and validating ends up turning on you. Initially, I thought it resulted from their poor self-image. Meaning, I thought they couldn't stand hearing good things about themselves or hearing their behavior reframed in a positive light because it felt like such a lie due to their profound self-loathing and inner toxic shame.
I also thought that sometimes it was a trust issue, i.e. their way of testing your love to see if you'd really would be there for them no matter what.
And then, you may be gritting your teeth with them because they've become so difficult and oppositional, so they also sense that tension they've caused by upsetting you or exhausting you emotionally.
And finally, because their attacking and "testing" can be so hurtful, you may either finally reach your breaking point and strike back (which will either REALLY upset them or make them victoriously happy that you finally broke down and have become inferior to them, as they perceive it) OR you may simply place healthy limits on their offensive behavior -- something they hate because it implies that they are wrong in some way and people consumed with toxic shame usually cannot tolerate being wrong or at fault.
And I still think those aspects are true, but I no longer think that's the whole picture.
I think that if they actually don't mean well or that they really are doing the wrong thing, yet you insist on repainting their bad stuff in rosy hues, then they sense that dishonesty on your part (however sincere your own intentions are).
Maybe you really do think they're just kidding about a negative thing they said.
Maybe you really do think they care about how their hurtful behavior affects their neighbors, their spouse, or their children.
Maybe you really do think they want to improve and do teshuvah, but are just struggling through a rough patch right now.
But what if they don't?
Maybe they don't. I made this mistake a lot.
Let's look at it through a parable...
The Bald Child Treated as a Thick-Tressed Child

Fine. But what if you start treating this child as if she already has a full head of thick gorgeous hair?
What happens if you decide to brush that bare little head with a hairbrush meant for long thick hair? (Ouch!)
What if you decide that you needn't put at hat on her when you go out in the sun because, heck, it'll just be too hot on top of all that thick hair? (Sunburn! Sunstroke!)
What if you decide to place barrettes and hair accessories on her head with no hair to hold them in place? (They'll fall off and get lost.)
It's very nice that you view your child in such a positive manner. But tachlis?
THE KID HAS NO HAIR! She's bald as baseball!
Forget her hair for a minute. It doesn't exist right now. You'll need to take her bald vulnerabilities into consideration, but at the same time, you can also focus on her positive qualities that do exist, like her gorgeous eyes or her astounding fine-motor coordination.
Stopping buying her hair accessories (except sunhats) and instead, buy her stickers for her adept little fingers and turquoise jumpers to accentuate her pretty blue eyes.
The Twin Transgressions of Chanifah & Lashon Hara
The Torah outright forbids chanifah, which is likely another reason why painting a person as too rosy a picture often leads to disaster for you, as described at the beginning of the post. Chanifah is a severe transgression according to the Torah and Ways of Tzaddikim/Orchot Tzaddikim dedicates a whole chapter to eliminating this quality.
If your love and good intentions lead you to sin (like the sin of chanifah), then you just won't have siyata d'Shmaya at your side, no matter how much you truly want to want to perform chessed.
Being smacked out of the relationship is Hashem's way of getting you out of a harmful situation. He loves you and doesn't want you to continue down the path of chanifah. He wants you to be good and reap reward, and not the opposite.
It should also be pointed out that very difficult people usually speak lots of lashon hara. This often occurs under the guise of doing so l'toelet (for a beneficial purpose), but they usually go far beyond the limits of toelet. They genuinely feel hurt, betrayed, and frustrated with several people in their life (and sometimes for good reason). But they don't just pour out their frustrations occasionally to one person in a disciplined manner; it's constant. It literally goes on for years with an ongoing variety of friends, relatives, rebbetzins, rabbis, and therapists.
So you end up listening to lots of lashon hara under the impression that it's l'toelet, but really it's forbidden.
So you might feel shocked, hurt, betrayed, or guilty when the person you've been trying to help finally turns on you. But really, it's Hashem acknowledging your good intentions and trying to yank you out of a spiritually harmful situation before it's too late.
Tips to Top You Off
- Find a REAL merit or a good point in a person...
- ...but don't invent what's not actually there.
- Realize there is beautiful soul-light underneath all the dark muck...
- ...but don't relate to the person as if that light is already shining through when there is really only dark muck for now.
- In other words, don't treat a bald person like a full-head-of-hair person.
- Daven for the person.
- Tell Hashem of that person's good points and good potential.
- Be kind and compassionate, but don't sacrifice your own soul or your Olam Haba for this person's ego demands.
- Review the laws of lashon hara and chanifah so you can identify them and follow them accordingly.
- Lovingly and cheerfully do your own cheshbon hanefesh to catch the sneaky traits that can trip up even the best person.
- frequency
- intensity
- duration
Why? Because we all mess up at times.
We all get frustrated, angry, negative, stressed, and overwhelmed.
We can all lash out with non-toelet lashon hara, yelling, and other forbidden behaviors.
So it follows that if someone engages in prohibited behaviors infrequently, without overwhelming intensity, and of short duration, then it would be wrong to judge the person according to this negative outburst.
When I discuss people who are behaving dysfunctionally and unremorsefully, I mean people for whom this is their normal pattern of behavior over the long term.
I do not mean people who are struggling through a low point in their life or undergoing serious stress at the moment. Even the best person can be knocked off kilter for a week or even a month. But if years go by and the person shows only superficial change or no change, then you need to take that into account.
Of course, a person can turn himself or herself around even after decades of bad behavior. It has happened. But until they do, you need to take their history of frequency, intensity, and duration into account.
___________
Related posts:
How Embracing a Contradiction Leads to Resolution
4 Things to Know about Beneficial Lashon Hara
How to Speak and How to Listen to the Lashon Hara of Hurt Feelings
May we all merit to do teshuvah from love and not from suffering.