Should I give my boyfriend a 2nd/3rd chance?

My bf has shown a pattern of being pushy/controlling if it's something he really wants and also seems to be unaware/does not care about my needs.

He can be egocentric (per my therapist).

Long story short...been together a couple of years and his pushiness really got to me and I told him I felt suffocated including living together and pushed around and needed a break. I know he feels bad when we aren't together but I'm much more independent and need my space. I think sometimes he was trying to get me to fill the gap after his divorce only a few years prior to meeting him.

Not sure how long a break should be but I figured a few weeks. Problem is we are invited to 2 consecutive weddings in the next 2 weekends and I just don't feel ready to give him another chance and not sure I ever wills so I told him I wasn't going to the 1st wedding of his friend and I was going alone to the 2nd wedding (my friend) alone. He freaked out - he has written me "love letters" via text and email, begged to meet and talk in person, sent me a dozen red roses, etc told me the only thing that's important is for us to be together and he'll do anything to make it work etc and he'll do anything to make me happy. He then said in his email he hoped that it resets the concerns and I'll still attend both weddings with him. I declined.

I told him I didn't like his selfishness a few months ago and he told me then to give him another chance and he'd change. He did get a little better at that issue but then the pushy/controlling part started in again with the living together and even sometimes making social plans like making dates for us to go with his friends before asking me.

We do love each other but am I kidding myself about his behavior? if we get back together is it realistic to expect he will get pushy in a just a matter of time or is it possible he will change.

Even though I have a therapist, I find that sometimes is helps to reach out to folks who may have actually experienced this type of thing. I just don't want to throw away a relationship it took a few years to build nor do I want to stay in a harmful relationship so I suppose want some reassurance if possible.

In any event, my bf is not contacting me per my request (and he is going to the wedding w/o me) but I do need to make a final decision soon since there's no point in dragging this out either way.

The email he wrote me saying he'd change was quite detailed and said essentially he'll do anything to stay with me...his "push" for us to live together will not happen again unless and until I'll be ready; he is willing to adjust his life so I'm comfortable, etc. While the email sounds great, I don't think I can trust him to actually follow through. I think he's just saying what he needs to now to avoid me leaving him altogether. But maybe I'm wrong?

The other issue is what I perceive as him feeling somewhat threatened by my adult children. He seems to feel insecure when I'm with them and not him, even though I've given him no reason to be that way. The email addresses this and states he knows my kids come first and he wants the opportunity to get to know them better so they don't feel threatened by him (but he doesn't address his insecurity).

I know there's no way to know for sure if the decision I make is the right one but I want to make the best decision possible for my own mental health.