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I’ve been friends with this guy for over a year and currently am testing the idea of dating him. He expressed interest in me a long time ago but I didn’t feel any physical attraction towards him at that time. We remained friends and continued to share a social circle.

Recently I found myself grow to like him more. He makes great conversations and takes good care of his friends. He also is very capable at work, driven and self disciplined. All positive traits I’m looking for in a relationship.

The problem is that it’s difficult to get him to accept a "no" answer to his ideas. I would have to explicitly reject his invite to a group event (not a date) both in private and in front of our common friends for at least 7, 8 times until he puts a stop to asking. I watched the same thing happen to our common friend but she said she’s okay to his behavior. Well I am not. I feel frustrated and disrespected.

I shared with him my concerns and he really took it well. He took some time to reflect and came back with a sincere and thoughtful apology for not seeing how his behaviors had impacted me. He also expressed disappointments that I would not give us a try in the past year. Overall it was a reflective and transparent conversation. I felt I knew him better and my feelings for him grew a bit stronger since then. However, his behavioral change is not really matching up. He is now visibly more cautious with his words with me but in action would still text me when I asked for some time to myself to attend to a stressful life situation.

That said, he’s still on my mind a lot and I’m thinking about giving it a try some time in the future. He is still interested in me and is single currently.

I found myself deeply worried about his boundary pushing behaviors though and whether I will be able to deal with it. Also, I’m not sure if there are deeper issues going on that would come up later when we get closer.

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

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.

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

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?