Have name changed for this. In danger of being a v v long post as want to get all key points in, but here goes ..
I have a male friend who is extremely smothering and clingy. Whilst he is fundamentally a decent person, the truth is I wouldn't have ever chosen to actively be friends with him, but over a long period of time he has 'forced' (maybe too strong a word), but let's say 'shoehorned' his way into my life.
On two separate occasions, I've told him he texts too much, is smothering, should stop leaving gifts/flowers/cards at my door. Etc. It was hard for me to be upfront like this as I struggle with boundaries.
Most of the time I ignore his texts- I feel rude doing this, and it plays on my mind and causes a bit of anxiety - but I do this because if I do reply, it becomes an endless stream of messages. I hate that, and I've told him I hate it.
Our children are friends. Occasionally we meet up. (We are both single). On the odd occasion that we do meet up, he oversteps boundaries eg holds my hand until I pull it away, etc. Often makes innuendos which my DC have picked up on. It all makes me uncomfortable. I don't like to be rude (I know it's just having boundaries) and always end up feeling either resentful or guilty.
I've gone through periods of more than a year not replying to him. It's always him who instigates. Often when I don't respond (eg to a text asking if I want to meet up), he'll then post a note through my door, with a gift of some sort, repeating the question.
If he knows I've got a cold or something, he'll post a load of painkillers, throat sweets , tissues etc through the door. I know lots of people might think that's so kind & thoughtful, but I've told him before to not do it. I feel he's overstepping. I feel constantly in debt to him in some way. I feel it's very controlling and manipulative.
He often drives down my road (it's not part of a necessary route for him). If on the odd occasion I reply to a text (he'll often just text about his day- largely I don't respond),. he'll end up sending me cringey (sorry but they are) goodnight messages. Often he does this regardless.
I have found him to be quite passive aggressive at times. Despite this, he's very much a 'martyr' type, portraying himself as almost saint-like.
Any time I do see him, I brace myself for the inevitable tale of some good deed or other he's done with verbatim quotes of shining praise heaped on him! It just makes me die inside.
There have been times when he's sent what I perceive to be nasty underhand digs- always after a period of me not being in touch. Eg recently he sent a meme saying "you're a c*nt' which he laughed off as just being funny. The feeling I get is that it's aimed at me.
I know some might say I'm unreasonable for being in touch at all, but I find it difficult, and I have told him in the past how I feel. Should I spell it out again? He's previously said (in relation to his marriage where he stayed for many years after his wife told him she didn't love him, causing her all sorts of mental health problems) that he 'doesn't give up'.
He remembers EVERYTHING. To an unnerving degree (I think I find this unnerving because I have a terrible memory). It just feels intrusive when he feels the need to ask how 'something insignificant and already forgotten by me' went. I just find him intrusive in general.
Would you just stop responding?