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What should you do about someone who cannot be reasoned with about their behaviour. I say "this is hurting me, please talk with me about it" but they keep doing the same amoral behaviour. It isn't an evil behaviour, but it is destructive and scary. What is skillful and compassionate, in this context, for the laity? There's nothing I can do about how they behave, and I cannot escape them, so do I just go with it, allow myself to be mistreated? Does anything in the Buddhist canon talk about advice for destructive friends, e.g. what sort of friends to keep and what to do if a friend slips up, etc.?

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The sutta which I remember as "the sutta of the six directions" has a lot of advice about what sort of friends to keep:

See also this topic about what sort of person to marry:

I don't know about how to correct a lay friend:

The Rhinoceros sutta suggests it's better to have no friend, than a bad friend:

Though the path it suggests is unconventional (i.e. "become a monk") it seems to me that there's some underlying ethos like, "don't be foolish" and, "behave in a way that is 'praised by the wise'". And "get expert advice", including about morality and know-how (behavioural techniques).

I can only guess what "destructive" behaviour means but in a lay context, perhaps you might seek advice from a medical doctors, addiction counselors and/or former addicts, family/relationship counsellors, and lawyers.

Given my experience I guess I can't advise you, about whether and when to keep them as a friend, leave, return, forbid, offer, accept, etc.

I would advise that maybe you might or ought to avoid enabling or supporting misbehaviour -- I don't know whether this is a good theory, nor even a well-framed or insightful description of the phenomenon, but if it's a true or useful description it might be an example of misbehaviour you should avoid:

In psychology, codependency is a theory that attempts to explain imbalanced relationships where one person enables another person's self-destructive behavior such as addiction, poor mental health, immaturity, irresponsibility, or under-achievement.

Even if you keep the relationship, I'd suggest that at a minimum you also need "association with the wise" who can be role model for you:

  • Upaddha Sutta (SN 45.2)

    As AN 8.54 points out, this means not only associating with good people, but also learning from them and emulating their good qualities.

I might be remiss if I didn't mention "love", the advice above about "good and bad friends" is categorical and (perhaps rightly) divisive -- but it's also good to understand the doctrine of the "brahmaviharas":

These four attitudes are said to be excellent or sublime because they are the right or ideal way of conduct towards living beings (sattesu samma patipatti). They provide, in fact, the answer to all situations arising from social contact. ...

The Brahma-viharas are incompatible with a hating state of mind ...

"Non-hatred" maybe doesn't mean saying "sure, whatever you want" so much that it leads to immorality. Perhaps this is a balancing act which a good parent (perhaps a good friend) must or will learn, being benevolent towards their sometimes-immature children.

It might also be worth understanding doctrine about "conceit":

  • I think it's major cause of conflict, according to Buddhism: Māna
  • This answer suggests that a partially-enlightened person can see more accurately ("true")

The latter may be related to The Arising of the Dhamma Eye -- which is related to morality:

one who has entered the orderliness of rightness, entered the plane of people of integrity, transcended the plane of the run-of-the-mill

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I think you should put them on a horse and send them away. But you will think, "that was an experience of mine, i will cherish it". Regardless, you can't be a permanent entity like you think or reason with. Still the gods should be kind and generous and protect us like space that was earth.

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