Old work friend messaging

So someone i used to work with years ago recently messaged me out of the blue, we communicated for a week and did tentatively talk about meeting up but I started to get weird vibes so backed off a little. Ive recently come out of a relationship and have been enjoying my own company so the thought of this potentially being a date did freak me out so I politely messaged him to explain and let him down gently that I wasn't interested in meeting up. He then ended up getting angry saying I hated him and always have and he doesn't like me like that plus I'd done this before (I told him I was not single years ago when he messaged then) and i should just be honest. I deleted didnt reply because theres no point adding more fuel to the fire. Anyway he messaged again calling me rude etc. So i replied trying to again tell him why and be polite. Anyway I eventually got an apology and he explained things going on in his life (he'd had bad experiences with relationships, been stalked, had anxiety) so again I was nice but he still was constantly asking me if I wanted to talk as friends and kept repeating this. Alarm bells were ringing for me so in the end I told him no and blocked him. I'm overthinking it now as I should have just said no and been blunt instead of trying to save someone's feelings so put my hands up i could of handled it better. Would love to know if anyone else has had this and how you got past it or dealt withit.

You've done everything right except block him earlier. You're much too polite to be wasting your time with people who abuse you because they didn't get their way. It's best to use plain English in short sentences when dealing with the like.

I've had two similar experiences as case studies (I'm a straight woman, for context, and these are both stories with straight men): 1)I had an old friend from high school reach out a few years ago, he wanted to meet up with me, we could never make the timing work out, but eventually I got the sense that he was hitting on me and I hadn't realized it. I told him something like "I'm sorry, I wish you well but I'm not really interested in getting reconnected." To his credit he accepted the rejection with grace, apologized, and never messaged me again. I felt bad that I had strung him along without realizing it, but ultimately I was grateful that we hadn't met up because it would have made things even weirder. 2) I have also gone on a date, told the person the next day that I wasn't interested, and suddenly been inundated with his demanding questions. "Really? Why? I thought it was a good date. Can you tell me what was wrong?" When I gave a brief, polite answer, he still wouldn't take no for an answer, so I stopped replying. To me this was clearly a toxic reaction rooted in him feeling emasculated by my rejection and/or entitled to women's time and attention. Hindsight is 20/20 so I wouldn't beat yourself up over not setting stricter boundaries before you even knew they were needed. I think you were right to listen to the alarm bells. Even if him asking to talk as friends was "genuine", perhaps he needs to learn a lesson about how he's coming off to people. In this case that meant being blocked. It's over now and I think you should try as much as possible to forgive yourself, forgive him for being a flawed human being, and move on. Be kind to yourself, do something nice with people you trust to get your mind off of it.