Burning Bridges

74jax

If you are only contacting him every couple of months, I'd be inclined to carry on. 
Just a simple, 'hi just letting you know I'm here for you, hope you're well' etc and leave it at that.
If he has issues he might one day appreciate that text. Or he might not. But for the sake of 1 text every 2 months is just keep sending it.
I wouldn't invest anything else in this, no money or time etc unless he indicates he's ready to go back to his he was before. 
I wouldn't even invest 'worry time', send your text, know you've sent a lifeline if he ever needs it, and move on with your day. You may find you stop sending the text, which is fine. 

nora_nora

I still think now that the OP can see this friendship isn't what she though it was, perhaps now is the time for an honest talk with herself about why she has clung to this for so long. A need to rescue other people often stems from a lacking elsewhere in your life. Maybe time to stop wasting energy on something that isn't what you thought it was and spend that energy on yourself instead.  He clearly doesn't see you as the friend you see him. 

Claddagh_Noir

I had 'friends' who were always full of drama.  All they did was complain about their children / boyfriends / husbands / work life etc.  They never asked how I was, they didn't even pretend to care.  I just felt like an agony aunt and it was sapping the life out of me when all they would do is moan about their lives vocally to me but bragged about their fake, happy lives on social media. 

 I had to cut them off when there were not there for me when I was bereaved a few years ago.   It is a shame it took the passing of a loved one to see how fake these so-called friends were. 

hb2

Slinky said:

Friendship will often fall into one of 3 categories. A reason, a season or a lifetime.

This. I have had friends I thought would last for life, but things changed. That doesn't diminish the friendship we did have, it just means that it is time to move on and find new ones.

pinkshoes

You clearly don't get anything out of this relationship, so why are you bothering??

Friendships come and go. People change, so make new friends and lose contact with old ones that they no longer have anything in common with. You tried to make him take path A (which seemed to be what you wanted) but he has chosen path B (which clearly he wants), so just move on with your life and focus on the people around you that do want to spend time with you.

Primrose

Sounds as if he,s the sort of guy who might wait util he,s in a needy position and then contact you wanting something you're honestly no longer really willing to give.
i,d just let things  die.  There,s little worse than knowing you're just being used And will then be dropped again so the longer the gap between contacts the easier it will be to make a permanent break.   As others have intimated, true friendships can last the test of time, even with breaks between contacts.  The insincere ones die a natural death. 

HampshireH

Had a friendship from 1st year secondary school. Got to my mid/late 20s and was so sick of instigating contact / being cancelled on I stopped. I realised I got nothing from the so called friendship and didn't miss that person. Proven by the fact they never got back in touch for years.

We have mutual friends so I always wanted to ensure it wasn't ever a big deal and would ask after them etc out of politeness if I knew they had met up.

I also sent the odd online message on their wedding day to congratulate and when there was a bereavement to offer condolences. 

We now, many years later follow each other on a social media platform and have interacted more in the last year (instigated by them) due to some similar experiences but I would never go back to anything more than the odd online conversation.

Move on. Time/life is precious you don't need to waste it on people who contribute nothing to yours.

ceremony

I'm going through this right now but I'm struggling to let go. It's someone who never reaches out unless they need something, but I know from our extended social circle he's like that with EVERYONE. He's terrible at maintaining friendships on anything more than a superficial level.

Over the years he's driven a lot of people away and I'm one of the last people he has left. He has moments of self-awareness when he realizes that it's his distance/aloofness/flakiness that has put him where he is today, but he just can't help but push people away.

He needs a lot of practical help right now and I'm struggling with the conflicting urge to help becaus he has no-one, or tell him where to go because he's taking a lot of energy and I don't have that much to give.

To the OP, if your "friend" is generally OK (not depressed, in trouble, etc) and has a social circle outside of you I think you can and should set boundaries now so that they can't guilt-trip you if they do end up in trouble later. Put yourself first, start saying 'no' to them sometimes and leave a bit of distance. If they continue wanting to be friends when they can't always get what they want, that's great. If not, then at least you know where you stand with them.

Bogof_OAP

LoveSauce said:

He hardly works anymore, would rather get drunk/high. He's a few bad months away from homelessness. And I honestly feel just because he has me (who owns his own house) that I'm some sort of contingency plan. 

Hell would have to freeze over before I let him stay with me.

I read this as the OP also being male (owns HIS own house), and also that I would steer clear of letting this guy know that you'd be there for him if he hit a bad time - that's the quickest way to have him land up on your doorstep.

To be honest I can't see that there is any point even keeping in touch with this waster - drink and drugs can lead to personality problems and you really don't want to get dragged down with him.  

Time to let go, move on and forget about him I'm afraid.  He was a chapter of your life but that ended some time ago.

nora_nora

Bogof_OAP said:

LoveSauce said:

He hardly works anymore, would rather get drunk/high. He's a few bad months away from homelessness. And I honestly feel just because he has me (who owns his own house) that I'm some sort of contingency plan. 

Hell would have to freeze over before I let him stay with me.

I read this as the OP also being male (owns HIS own house), and also that I would steer clear of letting this guy know that you'd be there for him if he hit a bad time - that's the quickest way to have him land up on your doorstep.

To be honest I can't see that there is any point even keeping in touch with this waster - drink and drugs can lead to personality problems and you really don't want to get dragged down with him.  

Time to let go, move on and forget about him I'm afraid.  He was a chapter of your life but that ended some time ago.

I'd agree. I think it's time to let it fade naturally into the background and stop wanting it to be more than it really is.