How to end a text conversation when they won't stop

I was mates with a guy and we would text all the time. He knew that I didn't want anything and just wanted to be friends but because I would reply to his messages I guess he thought I may one day be open to the idea of dating. Anyway I decided one day we just need to cut things off because he needed to move on and it was getting tiring having to reply even though I would heavily hint that I didn't want to talk. Short replies, late replies etc.
For the next few months he would message every now and again with some sort of reason and it got to the point again where we had to have another conversation. He said he could tell I didn't want to talk but he just couldn't give up and he'd never want the conversation to end.
Recently we bumped into each other on a night out and he messaged the next day asking if I had a good night and asking how things were. Then he'd do the thing where he doesn't reply very late at night so that he can reply in the morning and keep the conversation going til the next day.

I don't want to be harsh because we were once good friends and it's a bit unfair to make him think I never want to talk to him again. It's just I can't let this get into regular messaging again. I've been replying slowly and keeping them short, not asking questions etc. but he always manages to keep the conversation going, sending long thought out messages or questions that I can't ignore.

Agree with the above poster on this.

You need to be cruel, to be kind. Replying the way you have been obviously hasnt worked thus far. So now you need a different tact.

Either you say to him you can't keep texting/talking with him, as you feel this friendship isnt going anywhere, or you just simply stop replying.

Nothing else is going to work here.

Surly its better you're up front with him, so he knows this is going nowhere, rather than him keep on trying and holding out hope?

No I know, but I've been up front so many times. Had the conversation countless times of me saying we shouldn't talk anymore. He knows I have no interest in him but he wants me in his life regardless. Again I understand because I'd love to talk to some of my exes, just for that connection again. I do agree I need to be more harsh but it's difficult to completely ignore messages

No I know, but I've been up front so many times. Had the conversation countless times of me saying we shouldn't talk anymore. He knows I have no interest in him but he wants me in his life regardless. Again I understand because I'd love to talk to some of my exes, just for that connection again. I do agree I need to be more harsh but it's difficult to completely ignore messages

You're not doing him any favours whatsoever. He needs to move on from you, and he cannot do that if he is in regular contact with you. Trust me. He simply wont move on from you.

So for HIS sake... you need to end this. Just cos he wants a connection doesnt mean its right for him, or healthy for him (or you).

Either block his number for a while so you don't receive his texts, or just simply stop replying.

Sorry, there isnt many other alternatives.

Either he is so socially unskilled that he is not seeing your massive hints, or he is seeing them (but is determined to ignore them). But either way, you have given enough hints now (and so its time to get straightforward with him).

Tell him the situation exactly the way it is: That while you still want to be friends with him, his level of contact is too much (and a reduction in messages is needed if the friendship is not to become very strained).

Some people overstay their welcome, its a fact of life. So do you let them live in your house (while spiting them), or do you defend your privacy & property?
Some people are very needy for attention, its a fact of life. So do you spend endless hours trying to appease them (while spiting them), or do you draw a line somewhere and let them know that they're asking for too much?

If you are to stand up for yourself in life, you can't always avoid any potential conflict. There are will always be some people who (knowingly or unknowingly) take too many liberties with others. And such people you need to stand firm with: there doesn't have to be mal-intent involved on his part for you to justify protecting your time and comfort zones. If he's not taking the hint, you need to get to the point on matters.

You are also "castastrophizing the situation" (in that even though you haven't confronted him, you're already convinced it will end in a worst case scenario). I say be honest with him (tactfully), and take it from there on wards. Things will probably be fine, but if he does threaten to fall out with you completely because he can't handle you not giving him all the attention he craves, then he is someone you are better off without.
And you must be willing to stand firm in your word.
If the situation continues despite your clear underlining of your feelings, then be prepared to cut off contact with him completely (otherwise by continuing to tolerate his behaviour, you will be effectively condoning and encouraging more of it).

I know the answer seems simple but he was a good friend and we still have mutual friends.