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.

It is widely understood through many shared experiences that trying to 'change someone' will not lead to mutually beneficial results. Here are just two of the many articles written on the subject. These in no way specific, you can search 'can you make someone change' for similar, current results.

7 Things You Can Never Change About Someone

#3: Their bad habits

The difference between habits and all other behaviors is the way they are ritualistically woven into our lives. The fact that something like smoking or nail biting is such a part of how a person gets through their day makes it a much more challenging thing to alter. It’s not that these things can’t change – but if they are going to, that has to come from within the person with the habit, not an outside person who doesn’t like it. And when it comes to the really #dark habits and addictions, like booze and drugs, this is doubly true. No one is going to truly stop using something that hurts them until they want to. Keeping yourself in close enough proximity to their self-destruction means you’re liable to being hurt as well – decide how much you can take, let them know they are loved, but never keep someone in your life with the idea that you will “fix” them. That is just not how that shit works.

A longer explanation:

You Can’t Change Him So Stop Trying

"If you are, here are your options: you accept him exactly how he is right now and find peace inside yourself or you admit that you do not have magical transformational powers over other people and lovingly end 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 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, you might be setting yourself up for failure.

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 not relevant, partly because she is not you, but also because 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 could be very relevant, 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 need to ask yourself, "why is there a difference in behavior?"

   
   
   

   I am not saying that there is definite danger in this case, but it certainly indicates a need for caution, especially if the pushiness is only towards women. Take the following information as an example: Women accuse opera legend Domingo of sexual harassment. And, there are plenty of similar stories that have come out over the past few years in which this pattern of pushiness shows up. The fact that the guy you are interested in "takes care of his friends" is great, and a generally a good sign, but does not necessarily rule out the possibility of danger given how much praise Domingo gets for being "kind and helpful", etc.

   
   

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.

Based on what you have described and how you are presenting this, I get the impression that you, deep down, already feel that the answer is "No".

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

Are the "deeper issues" here specific to the pushiness? If so, then possibly (please see what I mentioned directly above). But, if this is a general concern, then it's not really a fair one because a) there is no way to predict, which is part of why we date (to get to know such things), and b) we all have deeper issues (every single one of us ;-).

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

Answer: To be clear, you communicating effectively does not guarantee any change in his behavior. Maybe he does change 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.

Still, you have already communicated your dislike of the pushiness. He has indicated a willingness to change, and it seems like he is already trying. The fact that he is not 100% there yet does not indicate that he won't get there. Habits truly are difficult to change, and some conversations will need to be repeated. There are requests that my wife and I have made of the other over the years that have come up several times. There are some things we can start or stop doing after only a single request, but there are plenty of other behaviors that will need some degree of reminding. The important thing is that there is effort being made to change behaviors that have been identified as truly important to the other person.

• If there are no changes and no effort made to change, that is clearly a problem. Don't waste time trying to change someone who doesn't want to change (assuming this is a critically important issue). It's a distraction that could keep you from being available (emotionally / mentally) when an obviously good choice presents itself.


• If effort is being made then perhaps some clarification is needed. In your case, you said that you needed "a lot of time", but that could mean different things to different people, so you could clarify by saying, "When I said that I needed a lot of time, I meant at least several weeks" (or perhaps "a few months", or even "don't call me, I'll call you").


• If he changes is behavior, then great. At least for now. And maybe forever, but not guaranteed forever. He could be changing just to get you to go out with him. Or he could have changed out of respect for your request, but might accidentally do this occasionally in the future.

I guess what this comes down to is: You need to be clear (as much as possible) with him and with yourself.

• First, with yourself: you need to figure out what is acceptable and what is considered too pushy, how important this issue is to you, and where your limit is if this is a critically important issue. It also helps to understand why you are making this request.


• Then, With him: you need to communicate specifically what you don't like ("being pushy" is a bit vague; the more he has to interpret / guess as to the meaning or specifics, the less likely it will be that he meets your expectations), why you don't like it (even if it's just "it's disrespectful"; this should help the person want to change, not just comply reluctantly), and if it makes sense for the situation, one or more possible alternatives. If this is a critical issue and it keeps coming up, then you need to communicate just how important it is and what you might need to do if it continues.

The only things you can control are you and your message. You cannot control his response, nor even his interpretation of your message. But, the more details you can provide will increase the chances that the message he receives is the message that you sent. For example:

• "Please don't be so pushy" might result in him asking the same question 4 or 5 times instead of 8.


• "Please don't ask more than once, though occasionally if something is really super important then 2 - 3 times might be ok. But always asking 2 - 3 times, or ever asking 4 or more times, is absolutely not acceptable." is much more likely to result in you getting what you want.


• "Asking me the same question over and over again because my answer was 'no' is disrespectful, hurts my feelings, and makes me think that you don't truly care about me. Please don't ask more than once...same as quote directly above" is much more likely to be a long-term change (fewer conversations about needing to change).

Communication is difficult. Good communication even more so, especially because we don't always know what we want, or why we want (or don't want) certain things. It takes extra time, energy, patience, and self-control to communicate effectively. "Don't be so pushy" certainly is quick and easy, but also far less effective. The extra effort is worth it, though. I have known my wife for 14 years now, and we've been married for 12 of them. We have 3 kids and our fair share of fights. And we are still quite happy with each other and how things are going.

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

Edit:

It may be a cultural thing. There are cultures where this may be part of their etiquette. In China, it's expected for a gift to be refused 2 or 3 times before being accepted. If you accept it right away, it's considered that you are greedy. It may also be considered rude to complain about the custom. I'm not saying this is what's going on, but it's something to consider.

Under section General Tips for Gifts-Giving in China:

Recipient often declines the gift while the giver has to inisit a bit. The recipient should not appear greedy when others give gift to him in China. So the recipient often declines the gift you give twice or for three times before accepting. You should offer the gift again after the recipient decline the gift, and he or she may finally accept your gift.

https://www.topchinatravel.com/china-guide/chinese-etiquette-gift-giving.htm

Also under section Chinese Etiquette #5 Chinese Gifts

Refuse the gift at least two times before accepting it.

https://www.taiwanese-secrets.com/chinese-etiquette/

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 don't think you are being unclear; I think he's simply refusing to accept your no for an answer.

In Mythcommunication: It’s Not That They Don’t Understand, They Just Don’t Like The Answer, the author quotes a 1999 study by Kitzinger & Frith:

Drawing on the conversation analytic literature, and on our own data, we claim that both men and women have a sophisticated ability to convey and to comprehend refusals, including refusals which do not include the word ‘no’, and we suggest that male claims not to have ‘understood’ refusals which conform to culturally normative patterns can only be heard as self-interested justifications for coercive behaviour.

If you dismiss this red flag in his behavior, there is no good reason to think he won't continue to push other kinds of boundaries, including sexual boundaries:

Finding love should never mean being uncomfortable and doing things you don’t want to do. We asked dating columnist and Kotaku contributor Dr. Nerdlove about dating red flags, and he recommends you watch out for “boundary-pushing behavior”:

“You tend to see this most often around sex—someone trying to convince you to do things you’re not ready for or interested in yet—but it can show up in a number of different ways. It can be as obvious as ignoring soft NOs, or not stopping when asked, to demanding reasons why. One way people will try to push boundaries is to use silence and disapproval, sometimes known as a ‘freeze-out’ in order to get you to agree to what they want.”

It sounds like you are already concerned about this, and I would listen to that warning in your head:

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.

He is telling you what kind of person he is; this is a "red flag" warning: my advice is to shut the door on a relationship with this guy permanently.

My first impression (as a mid-20s man married for four years, so hardly an expert) is first that you had quite a mature response to the whole situation to start with. Just approaching him with the boldness to be honest about how his behavior makes you feel has been difficult for me to learn how to do. So kudos.

I think it may be less because he doesn't care about how you feel, and more because he a) really wants you to be there because he likes your being around, and because b) he wants to communicate to you that he likes spending time with you. I have a feeling that what's motivating his behavior are mainly good thoughts and desires, and he just needs to be made aware of where he's succeeding in what he's trying to do and where he's not.

Of course, I don't know his heart or the nuances of your relationship and conversations. It's easy for me to want to give the benefit of the doubt on both sides, and I think its helpful in a relationship (one that isn't apparently abusive) to try to give the other person the benefit of the doubt when it comes to their motivation.

That being said, you've already made him aware, and he still hasn't really fixed the problem! My thought there is, like others have already said, that he is probably putting in effort to do better and just needs more direction. Also, I recommend trying to remember that in your relationship you may end up inadvertently doing things that affect him negatively without realizing it, and then after he tells you how it makes him feel you may put effort into doing better only to have him tell you, again, that he still feels hurt by something you're doing. I think that as long as you continue to see him trying, that shows that he values you. And I think you both having grace for each others' failures is a really significant way to show love for someone. Of course not to the extreme of putting up with abusive behavior, but it doesn't sound like you're in danger of that in your situation.

So the advice I would give is that this is the most important thing: decide whether his current behavior is below your minimum standard of what you can live with. If it isn't, then continue to communicate to him how it makes you feel not expecting or demanding that he change his behavior, but just being honest about how you feel. I think it really helps to reinforce acceptance between two people when you don't make it sound like your acceptance of them depends on their behavior. Of course, it depends on how serious the behavior is to you. If it really is unacceptable, then I think it's important to tell him not only now negatively it affects you but also how serious of a deal it is to you, and it may help to bring a friend into the conversation to reinforce your perspective.

I wish you guys the best, and I hope my words are encouraging and are not hurtful.