16 days no contact

My boyfriend of 5years ended things last year because towards the end we argued alot. He said he needed space to think about his life and career but the relationship was too toxic for him to do that. I pleaded for 5 months to no avail. Then i let him be. On the 6th month he came back and we picked up from where we left off (biggest mistake ever). In my eyes he had changed alot so i felt insecure and went back to being needy and clingy. He started passively ignoring me and didnt want to be around me much, he told me that he didnt know if he wants the relationship, all he knows is that he loves me more than anything thing else. I was hurt but i kept pushing. One day i told him i didnt like the way i was being clingy and needy because he was giving me little or no attention. He apologised for making me feel that way and said his head hasnt been in a good place. (He struggles with depression and has been working hard on his career)Eventually i told him i was going to let him go because he didnt seem like he wanted a relationship. He agreed with me but asked us to remain lose friends stating that nothing but death is an assured end to things. He later asked if we could talk at least indepth. I first turned him down because i was scared of what he wanted to say. Later then i figured it might not be bad news afterall but instead of me to wait till he was ready, i tried to enforce a meeting (which was just three days after i “let him go”) and as expected, he ignored. The next week was my birthday and the night before the day, i sent him a message telling him i didnt want to let him go unless it’s what he wants. And i’d like to know how he feels. If he wants a breakup, it’s fine, i’d take it. But if that isnt the case then we could work things out. I felt i was sitting in a limbo with him.He didnt respond. The next day he called me to wish me a happybirthday saying he read my message but slept off immediately because he’s been on strong sleeping pills. And said he would respond to it later…he didnt. Sent me a text later in the evening asking how my day went, i told him it went well and that was it.
I decided to break contact because i felt bad about how needy i was. During the first breakup, i tried to be a better person for him instead of being a better person for me and i fell right back to the beginning. I did NO CONTACT this time so i could heal and focus on myself and tell myself that life does not end with him. I did it to regain the confident and awesome person i once was. I did it to find myself again. It’s been 16 days of no contact and he has reached out to me 3times (first was 4days after my birthday, then 2 days after that.) I ignored the first 2 because i felt i wasnt yet in a right place to respond. Last time was 2days ago and i responded because i felt better. He sent a picture of job opportunity i was interested in 3years ago and i laughed about it saying it was years ago and bigger things now. He asked if i was good and i said “sure, i am. Thanks” I feel like i am in a good place now and i can handle things better. To be honest, i dont want to go back to the old relationship. i’m hoping for a new one with him. Which is starting as friends and evolving from there. I want him to feel safe and free, not tied down to me, i also want to use the medium to keep finding myself and refrain from being clingy and if our friendship becomes strong enough to grow further, then good for us. It’s been 16days of no contact, i feel i am ready and he has reached out to me 3times. Do you think it’s time to break it?

You’ve chased after a man who apparently doesn’t want a relationship. If he wants to work through the problems with you, the two of you have to be willing to discuss it and make the changes needed in order to have a healthy friendship… maybe leading to a reconciliation. Good luck.