Mdthbs

I routinely deal with people who are pushy and are constantly testing boundaries. Like you, I find this behavior annoying.

Also like you it seems, I don't really mind this behavior in social settings, it's just who who these people are and having excellent interpersonal skills myself, have no problem dealing with them.

Here's where I think things are going off the rails.

However, his behavioral change is not really matching up...

to your expectations.

You should first come to terms with these expectations and decide if you can successfully negotiate this internally and accept his behavior, otherwise, it will be a constant source of conflict.

There is a somewhat common saying that goes (please substitute your appropriate gender roles) "A woman chooses a man thinking she can change him, a man chooses a woman hoping she never does." This is meant convey the futility change expectations. Which leads to your question...

How should I preempt the potential conflicts and communicate with him effectively so that he could change his behaviors?

You can't/should't/or it's very very difficult. (This is a frame challenge but, it's based on OP's description, please read carefully.)

You've already spoken to him about this with some noticeable results, yet you're still not happy with these results. You describe he's "visibly more cautious with his words" which implies he's using conscious effort to accommodate you.

What this means is, you can preempt potential conflicts by merely talking to him, but the risk is you both will find this effort unsustainable in the mid to long term. Meaning, you will have to continually express your concerns and he will have to continually work to accommodate them. This can become tiresome and a distraction to the relationship.

I used to have a friend who wanted to date me, but I wasn't interested. He made a number of attempts to get me to sleep with him, especially when I was alone at his house, drunk, and emotionally vulnerable. I finally said to him, "I've already told you I'm not interested. If you value my friendship, you'll stop asking." His answer was, "Well, I want to be with you, so I'm going to keep pursuing you." That was when I decided our friendship was over.

Your guy is a better manipulator because he knows how to say the right things, but the proof is in the behavior. If he had really heard you and taken in what you said, you would see a change in his behavior, and you haven't. That means that, fundamentally, he doesn't respect you or care about your feelings. I especially don't like the subtle attempt to blame you for his attitude because he was disappointed that you haven't started dating him yet.

The problem isn't that you haven't "communicate(d) with him effectively so that he could change his behaviors." The problem is that he enjoys pushing boundaries and he will continue to do so as long as it is tolerated. I think you're better off without this guy in your life.

You sound extremely cautious when you say things like

I found myself deeply worried [...] whether I will be able to deal with it

and overly objective when you observe that

He also is very capable at work, driven and self disciplined.

More like assessing an employee than dreaming about a romantic relationship.

Are you sure this is the right basis for a date?

It all depends on context of his action and context of your expectations. Let me explain.

• If this was one of your non-romantic friends who did this, would you find it as annoying?

Consider what his question is and whether you are saying "no" because you don't want to do it, don't want to do it with him, or don't want to do it because it's him asking. I'm not saying you are wrong for saying "no" in any of those situations, just be aware of your real reasoning of your answer. He may have a different idea of why you are answering "no" and trying to get around your initial answer, thinking you'll decide it's best and "go along" with it. Whether it's actually better is entirely dependent on the situation.

Example:

Him: "Let's go to a snake farm."

You: "AAACK! No!"

Him: "But I love snakes."

You: "No!"

Him: "Don't you want to get over your fear of snakes?"

You: "Yes....."

Him: "Then let's go to a snake farm."

You: "No!"

This is pretty clear. You have a clear "knee jerk" reaction to snakes and don't want to go. You still what to get over your fear of snakes, but that's just too much right now. It may serve you better in the future to know what snakes are dangerous, which are helpful, and how to act when/if you meet one in the wild. But you're just not ready for it right then. Maybe you don't want to give him the satisfaction of seeing you freak out and constantly squirm at being around snakes.

To be clear, I'm not saying all interactions like this are clear or healthy, let alone have a benefit of learning something. But you need to figure out if the request follows this format or not.

This is crucial to figuring out if this is him being manipulative. Even if he is manipulating you, you have to figure out if it's because he wants to help you or help himself. Constantly helping himself is not good for you. Constantly helping you can be annoying, but it's coming from a better mindset.

• Is he asking in a way that he believes will be taken as humorous?

To exaggerate a question is sometimes taken as humorous. Let me reuse the last example.

Him: "Let's go to a snake farm."

You: "AAACK! No!"

Him: "Please, please, please, please, please, please, please, please?" {Puppy eyes} {Protruding lower lip}

Done occasionally, this is generally considered fine. However, over using it constantly is definitely a problem.

• Do you do this to him and how often?

Example:

You: "Let's go to the club to dance."
Him: "I'm tired, so no."

You: "Aw, com'on, we don't go anywhere anymore."
Him: "No."

You: "But I want to go dancing with you!"

Him: "No."

I'm not saying that him asking you is more, less, or equally annoying or unfair, I just want you to think about how he sees you and if he's just trying to act the same way to you as you do to him. I'm not saying this is your fault, I'm just wondering if maybe he thinks it's ok for him to do it.

However he is asking, the fact that you talked to him about it is a good first step. You say he is responding to your conversation, which is also a good first step. It takes time to change habits. I'm not going to make excuses for his actions, but he may have had reasons for thinking re-asking was ok and now needs time to unlearn this idea.

I had a co-worker that literally used the word "literally" in every sentence, literally every day for literally every thing he talked about, and sometimes literally multiple times in the same sentence, even when it literally didn't make sense to literally use it. Literally. Yes, what I just explained and demonstrated was how he talked for several weeks, until someone mentioned it to him and how annoying it was. Especially when he meant "figuratively". It took him a while to change, but he did.

Give him a chance to change permanently. If he doesn't then you have a problem. Even if he does permanently change and he still does it on occasion, try not to be mad about it. Just remind him you don't like it.

Also, is this really a "deal breaker"? Everyone has their faults. You just need to figure out if you can live with this one or not. You also need to figure out if it's manipulative and if that is actually harmful to you. This is your preference and no answer is a wrong answer, unless you can't live with the answer.

"I'm a man, but I can change, if I have to, I guess." - Red Green

https://en.wikipedia.org/wiki/The_Red_Green_Show#Conclusion_and_credits

It seems like you are doing a great job of communicating openly and honestly with this person, as well as being honest with yourself about your needs. However, I can't help but feel that you are mostly setting yourself up for failure, and not just with this guy.

I watched the same thing happen to our common friend but she said she’s okay to his behavior.

1. Your friend's opinion here is irrelevant as you two are not considering the same type of relationship with this guy. It's much easier to be forgiving of faults in friends and acquaintances than in romantic relationships.


2. The fact that he is treating another woman this way is not irrelevant, especially if he does not behave this way with male friends / acquaintances. Have you seen him behave this way with men and women, or just women? If it's just women then you can stop right here: hard-pass, move on, next, (you get the idea).

I found myself deeply worried about his boundary pushing behaviors though

Let's stop right here. A romantic relationship, by its very nature, is where a person is most vulnerable. If you have any misgivings about trust and safety, is there a reason you are still considering this? It's one thing to not know and to take a chance to find out, but to already have an inclination in this direction seems a bit troubling. Especially when it comes to boundaries. If you do start dating, then if you decide in the future that things aren't working out, do you feel confident that you can end the relationship (at which point you will be more emotionally invested and less able to withstand someone who is pushy, and might be pushier in private than what you have seen in public)?

and whether I will be able to deal with it.

I think it's pretty clear at this point that the answer is already "No!".

Also, I’m not sure if there are deeper issues going on that would come up later when we get closer.

Well, you just described a concern shared by 100% of people on this planet. It's also something that you cannot really predict. There are people who do not have clear boundary issues that still have "deeper issues" that you will only learn about upon dating for a while. Along those lines, who is to say that you are not the one with "deeper issues" that he should be worried about? I mean, this conversation right now is entirely from your perspective. Meaning, this is a concern, but not specific to your situation.

Question: How should I preempt the potential conflicts and communicate with him effectively so that he could change his behaviors?

Answer: you cannot. Not much can be predicted with a high degree of accuracy. That's just not how things work. We take educated (if possible) guesses and try our best. Maybe he does change this behavior for the better and maybe that is a permanent change. What then? That is no guarantee that he might not have some other objectionable behavior you are currently unaware of. It's not a guarantee that he won't develop an objectionable behavior in the future. It's not a guarantee that you won't change in the future such that you view a particular behavior as objectionable that you currently do not view in that way right now. It's no guarantee that you won't change your behavior in some way that he will find objectionable.

Given all of the above, it seems like you are working too hard at trying to find a way to justify dating this person. Should it really take this much effort / convincing? Stop wasting time trying to fit a square peg through a round hole. It's a distraction that could keep you from being available (emotionally / mentally) when an obviously good choice presents itself.