What is his game?

[TreacleScoooone]

First time posting so please bear with me, will keep as brief as possible.

I met a friend 12 years ago when we both ran businesses, I booked his business for services needed by my business & we became really good friends & now know each other’s families very well. I am now 40(F) & he is 59(M). He has been married nearly 40 years & I am also friends with his wife albeit not as close as I am with him.

We have fallen out quite a few times now because of his nastiness & attempts at manipulation but he always hunts me down via my adult daughter by sending her huge paragraphs or via our very few mutual friends. I am very much ready to cut ties altogether due to recent goings on but know he will do the same again so am going to have to ask my daughter to block him.

He has always made jokes about my weight even though he’s morbidly obese even after having a gastric sleeve & now being on the jags. The latest thing he’s started doing is every time I disagree with anything he says or have any opinion of my own he says “see THIS is why you can’t get a man” & his wife even said the same thing to me on a night out when I complained about a member of the bar staff being rude.

Last night him & I were running errands, he gave me a lift to get things done that I needed to do here, there & eveywhere & he came out with, out of nowhere “you do know no man will ever marry you don’t you?” followed by “no man will ever have you” to which I replied, “I don’t want or need a man & I shouldn’t just accept one that pisses me off just so I’ve got one and WHY are you so obsessed about my love life or lack of” - he has now started calling me a spinster whilst roaring & laughing his head off.

I know he gets a kick out of deliberately trying to ruin my self esteem & he thinks he’s fly but he really isn’t, I can see when he’s saying things to either hurt me or wind me up. I’ve even told his wife how he speaks to me & she just says to ignore him.

Twelve years of friendship, he’s been good to me as I have to him but it’s like he hates me deep down & when I try to cut ties he just tries to hunt me down. What I want to understand is WHY? It’s quite obvious he cannot stand me so why won’t he just let me be? Never known someone to be as nasty as this, get a kick out of it but then come begging once I inevitably lose the rag & tell him to sod off.

Excuse spelling errors it won’t let me click back to change them.

Because bringing you down makes him feel better.
This man is no friend and has no respect for you or your boundaries, cut ties.

He's a toxic nasty bully and you should get rid of him. You should get your daughter onboard with blocking him too. Explain how he belittles you all the time and that you've had enough.
Otherwise cut him out of your life, and ride out his attempts to use your daughter.
You deserve better friends.

He is not your friend.

He is not your friend - you said you have fallen out with one another lots of times - surely you can see that things aren't going to improve and he's not magically going to get a nicer character/personality?

You can't tell your adult daughter to block anyone - that's up to her - but you can absolutely tell her that you are no longer friends with him. Then you tell him that you no longer want to be friends with him - and tell him why - and then block him yourself.

I'd text him a final message before you block him so he doesn't start bothering your family and friends of what happened. I'd just say: Our friendship worked at one time but it no longer does. It's best we go our separate ways.

Then don't wait for a response. Just block him. Tell anybody mutual what you've done and that you don't want him having any access to you in any form. And also that you don't care to hear news of him, nor anything he's said or asked about you. You don't need his ugly presence in your life in any form. He's a sadist. Take care.

He’s a piece of shit.

He hunts you down because he wants to continue being a piece of shit because that’s what pieces of shit do.

I have done that many a time, the first part you suggested. It ends up in a tirade of abuse from him which I replied to last time by saying if that’s what you think of me why do you keep coming back? He is exhausting and draining. My daughter has said she will block him.

You can't get a tirade of abuse if you block straight away. It's literally as @ScorpionLioness79 said - send that message then block everywhere immediately. And breathe a sigh of relief! He has a point though - why do you keep going back? You really need to make this the final time you communicate with him - don't falter, your self-esteem is worth so much more than this.

Sounds like a weird relationship all round, why does he speak to/message your daughter? Can't understand why both of you haven't blocked him already.

Strange

It was me who asked him if he thinks so little of me why does he keep coming back, as in when I say right that’s it no more, you’re talking to me like crap I don’t want anything to do with you anymore he comes at me with a tirade of abuse & then I say to him well if that’s what you think of me why do you keep trying to make up with me via other people?

I know that seems strange but he doesn’t message her unless he can’t get hold of me or if I’ve blocked him/fell out with him. He doesn’t message my daughter regarding anything else. My daughter knows him very well & his son, they were at the same school. He is not messaging my daughter in any creepy kind of way.