How do I encourage my ex to set some boundaries with me?

If you weren't anonymous, I would memail this to you. I'm sorry that it's not a direct answer to your question. I couldn't help but notice the way you describe yourself in your question. You use extremely negative, loaded language: "psycho," "looney tunes." You characterize yourself as a horrible burden and you rush to "understand" people who don't want to be there for you ("dumped" on). I think this is not a separate issue from what you describe. It's hard to set healthy boundaries and stand up for yourself when you have such a negative self-image. This also doesn't really sound to me like, on his end, it's about you violating clear boundaries. It sounds more like he treats you as kindly or as unkindly as he wants to, resulting in a random array of reactions to largely consistent behavior on your end. You want him to tell you what you're doing wrong. Nothing. He is just choosing not to respect you when that's easiest for him. That should prompt you to set your own boundary which, as most commenters have suggested. To protect yourself from his unkindness.

Some people feel far too intensely about one another (love or hate) to be good friends. It sounds like you feel this way about your guy friend, and until you can cool those feelings down, where you feel little to no anxiety about basic interactions and aren't constantly using him as your emotional outlet, I don't think that friendship is going to work out between the two of you.

You can start by setting that boundary for yourself and not talk to him in a month or two. Your relationship does not sound healthy at all and much more time needs to pass before a healthy one is possible.

Stop asking him for help. Don't ask him to move things, process things with you, or otherwise give you stuff/assistance. I used to get pissed when my ex would ask me for advice because it felt like he wanted to treat me like we were dating but take zero responsibility for anything and have zero commitment. It would piss me off. Not every time, but sometimes, because I'd start feeling used after a certain unpredictable threshold. So yeah, stop asking him to help you with shit. It's not appropriate. Stop going to him for emotional support. Not appropriate. Go to movies, do things that are fun for BOTH of you.

Yes, you set boundaries for your own comfort. You don't ask others to set boundaries, because you don't know what's truly going on in their head. You can't solve your discomfort by telling him he needs to use boundaries better. The responsibility for protecting yourself is on you. (Is the phrase you're looking for "I feel uncomfortable calling you because it sometimes seems like you say yes to helping me, when really you meant no. Am I reading the situation right? Because I wish you'd just say no when you mean no.") It sounds like you just learned how to use a certain tool, and you now see ways he could be using it, too. But you can't expect others to deal with a situation using exactly the tool you would use. You might remember that you're still gaining new tools yourself, and anyway, it's their own "house" to maintain how they see fit. In addressing any discomfort you feel, it would be better to speak from your subjective experience ("I feel a bit uncomfortable because...") rather than speaking from an omniscient perspective ("you fail at setting boundaries, try harder"). You'll run into this question again in your life. As you keep doing your emotional work, you'll gradually become better than many people at naming your emotions, setting boundaries, and so forth. The best thing to do is to make friends who have good emotional and psychological skills. It's across a boundary or more precisely, "all up in other people's business," as well as rude, to be auditing their use of boundaries, etc. If they want to gain new skills, they will ask your advice or start therapy themselves.

I don't think ultimatums are the best way of asking for most things, though, so... Ultimatums are not the best way of asking for most things. But when you've tried to work a problem out with someone in all normal ways, and you would rather not interact with the person anymore than continue to put up with the behavior, that's a perfectly fine time for an ultimatum. I think http://ask.metafilter.com/187082/How-do-I-encourage-my-ex-to-set-some-boundaries-with-me#2693612 that I wish I could favorite it more than once. As to this: Hell, even he's said I'm doing nothing wrong, but he denies that he's disrespecting me. One thing I've noticed in my long and varied experience with people who treat others badly: if the person isn't treating others badly on purpose, or is unaware of it, they will be surprised, will feel bad, and be eager to make amends when it's pointed out to them. To me, when someone *denies* it, that's a sign that they are doing it deliberately and don't want to change, that they're getting something out of it. I wouldn't be surprised if this guy gets something out of being suddenly, inexplicably upset at someone and having them chase their tail trying to make him happy. After all, if he didn't enjoy that, why would he be uncooperative when you try to find out how to avoid making him upset? I don't know, man. This situation sounds a little toxic for you. Whatever his good points are as a friend, I think you can find a friend with all the same good points who doesn't toy with you emotionally and play weird control games. I kind of want him to say he's okay with my hanging up If you get into this thing where you're desperate for emotional validation from someone who kind of gets off on withholding emotional validation, you're only going to become a more and more desperate person.

had a violent alcoholic dad homeschool me, ....And you're asking your ex to set your boundaries for you. Do you see a pattern? Setting boundaries is a thing you do for yourself. You can't ask someone else to set them for you, although it's perfectly reasonable to ask them to be honest when they feel you've violated theirs. But as you've seen, people are not always consistent (or rational) in their boundary-setting or -keeping, which leads us back to you being the only person who can set and keep your own boundaries. Sometimes it takes a long time to become true friends with an ex. Sometimes it never happens. Acting as if you're just ordinary friends with no romantic or sexual history when you're just not there yet emotionally only makes the get-to-friends point take longer and be more painful. This is why lots of people, including me, are going to tell you to cut off all contact for some fairly lengthy period of time (at least six months). You both need to reset your expectations - especially the ones you're not really conscious of having - and redirect your emotional energy elsewhere.

http://ask.metafilter.com/187082/How-do-I-encourage-my-ex-to-set-some-boundaries-with-me: Beyond that, I really need a clearer set of boundaries from him if we're going to be friends. You are doing this totally wrong. You need to set boundaries, and you need to set them with yourself. For a start, stop looking to someone who has continually failed to give you the support you seek for support. That's a good boundary to make and to enforce with yourself right there. And for the record, he has expressed his boundaries, repeatedly - you appear to either not be hearing them or ignoring them. He has straight up said "I can't do anything about that" and said it often. How much clearer do you require him to be? "I can't do anything about most of your problems, so stop telling me about things I can't fix because that's not my job anymore and I don't want to do it." Does the extended remix version play more clearly for you? It doesn't mean you can't be friends but honestly you seem way too emotionally entangled to make that work right now. Take a long-assed break and don't make contact again until you have a life that is functional without him. It is not appropriate to rely on him for emotional support, not least of all because you apparently can't. That's OK. Different friends fill different roles in our lives; some are good for some things, others for other things.

You set the boundaries for yourself, not him. If he's not the supportive person you need him to be, then he needs to not be part of your present life anymore and remain part of your past. And, stop calling yourself looney tunes or psycho or whatever, that's never helpful.