Need advice abut my friend

I have a male friend, "A", who is thirty five years old and I've known him for about thirteen years now. We were originally just acquaintances, but back in 2009 we both came out of a really bad relationship break up. A asked me if I wanted to be friends with benefits. So we were hooking up, but we hung out and got to know each other a lot too. We were developing a really good friendship, so I ended the FWB. A was fine with it and we continued to be close friends and hang out and chat on the phone a fair bit. A told me that he could really open up to me the way that he couldn't to his male friends.

This went on for about three years and I personally considered A to be my best male friend. Then I became acquaintances with this girl and A met her through me. He became really infatuated with her and kept chasing her for a year, but she kept rejecting him. He also met my female bestest friend ever, B, through me. He started dating B, but the other girl got really jealous and told him to end it with B. So he ended it and he began a relationship with the other girl. He was in a bit of an on and off relationship with her for about 4.5 years.

The girl is actually quite awful and she was extremely controlling of A. She told him to end his friendship with me. Which I kind of understood, as A and I used to hook up and he had also dated my best friend. But the issue was that the girlfriend was extremely controlling and jealous about him hanging out with ANYONE, even his male friends and even his family (she didn't like his family for no reason). So A had basically dropped off the radar, but to be fair sometimes he still wanted to catch up with me in secret. The thing that I was finding a bit annoying is that A kept saying how unhappy he was in that relationship and he did try to end it a few times, but he always went back to that girl. Mostly he would only contact me when things were going really badly with her and he wanted my support, which I would always give. A had also cheated on his girlfriend with a colleague at work. So basically the friendship was bordering on non-existent for four years.

When A's relationship with that girl was coming to an end, he started seeing my best friend B again. But he was still kind of with the girlfriend, so he cheated on her again. He was seeing my best friend B for about 1.5 years, but B was actually not into him as a person and she only wanted sex from him and to only be FWB. She did tell A this and she kept it very casual, but he had very strong feelings for her and it was very obvious he wanted to be with her. The thing is that A has very low self-esteem and acts like a doormat and is very easily controlled. My best friend treated him pretty bad at times, where her and I would be out clubbing and she'd be trying to pick up other guys. Then if when the club was closing at 3:00 a.m., she didn't end up with anyone, she would booty call A and tell him to drive over and come get us and give us a lift home. It was usually about an hour drive for him and it was very late, but he would basically always do it and come pick us up.

The thing that bothered me about this situation was that when A ended with his ex-girlfriend, I was really glad to have him back as a friend because I'd missed his company. But almost straight away he started seeing my best friend and I was really made to be "piggy in the middle". A would keep asking me questions about my best friend all the time, like is she seeing other guys, what is she looking for from him, what is she doing, etc. I never lied and said she only wanted him for FWB, but I strongly encouraged him to actually speak to B directly and not keep asking me. Other things that A would do which annoyed me was that he would flirt with me or hit on me sometimes and it was obvious that was because he wanted me to tell my best friend about it and make her jealous. Or he seemed to be lying that he was seeing other women (sounded fake) and he wanted me to tell my best friend also to make her jealous. And sometimes when A was angry at my best friend because she treated him badly, he would actually take it out on me and snap at me and stuff like that. I always acted supportive to him and was there for him and even told him he can do much better than being treated like this.

Another thing that kind of bothered me was that A would always complain about his job for about eight years and say he hated it, but yet he would never look for another job or do anything to change the situation. And he would also always talk about this ex-girlfriend he'd always had a thing for since he was a teenager, but she never wanted to be with him and only would come crying to him after other guys used her and treated her badly. And he would always be too available for her and be her little puppy dog. I would give him advice to stop chasing that ex and to stop chasing my best friend and find a woman who loves him. But he would just always ignore my advice and just kept carrying on like this, but would always complain to me about all these things and wanted my support and for me to comfort him.

Then my best friend finally ended it with A. I was having a Birthday party and A said that he would come. Then he didn't come to the party and didn't wish me a Happy Birthday. Then I noticed that he'd deleted me off Facebook all together, without any message or explanation. I heard nothing whatsoever from him for six months and then at like 4:00 a.m. both my best friend and I got a drunken text from A saying; "I miss you both xoxoxo". I was annoyed with him for his behaviour, but two weeks later I did reply and we started chatting. He didn't apologise or anything for deleting me and just said that he was really angry at my best friend and he wanted space. I said that he should have just told me he needed space and just explained himself but he didn't seem to feel bad about it. Anyway, so we got back in touch but then he kept messaging me saying things like: "Tell your best friend I want to see her". I told him to message her himself and not keep asking me, so he contacted her a couple of times and she ignored him. But he still asked me a few other times to make her talk to him. I was finding this really annoying because he said that he'd deleted me from Facebook and ignored for six months because he was trying to move on. He has also asked me to never discuss my best friend, which I totally respected and never discussed her.

Then he said to me that he was finally dating that ex-girlfriend that he had always been obsessed with and that he was in love with her. But that he was trying to keep it only casual because she actually had a small child now from another guy and A had a problem with that. One time he texted me and asked how I was. I said I was having a really bad time at work and he basically ignored what I said and just began talking about that ex he's in love with and that he needed advice. I gave the advice to give it a go, despite her having a kid, because he had always had feelings for her. I think he didn't like that advice or something because he just really abruptly stopped the conversation and then I didn't hear from him for ages.

Another thing was that I'd invited him to my engagement party and he said he'd go, but then didn't go and later just said he got the date wrong.

Also he suffers from depression and every time I'd suggest getting therapy or getting some kind of help, he'd just ignore it. Or be defensive and like: "You know, you could message me more, I'm depressed!" But not really acknowledging all the support and advice I'd already been giving.

I was getting sick of his behaviours and felt a bit used and like A only wanted to be my friend to help him with his girl dramas. So he texted me a couple of times and he also messaged me through Facebook messenger, but I actually haven't replied. This is mostly because I'm not actually sure if I want to continue the friendship and how I feel about him anymore. He also keeps messaging my best friend, even though she basically doesn't reply and she also told him that she doesn't want to see him and she has moved on. I do realise that his relationships with women are none of my business, but I'm just tired of all his drama and I'm not sure what exactly I'm getting out of the friendship. I find some of his behaviours immature and not the way a 35-year-old would act.

Do you think the friendship is pretty much dead now or should I maybe give it another chance?

It doesn't seem like it was ever a friendship and you know it. He just talked to you when he needed something. Trust your instinct, it's spot on.

You've outgrown this friendship. Just get busier and busier and briefer and briefer with contact. Sometimes a slow fade can create boundaries without burning bridges or having confrontations.

So, basically , you considered him a friend but he never considered you to be a friend.

Meaning there was never a friendship between you , just convenience. Initially it was convenient for both of you but for the most part just convenient for him. That’s not a friendship.

Yeah, I know you guys are right and I was thinking the same. That's why I didn't reply to his last few messages and I've just been thinking about what I want to do. But my gut is telling me to just slow fade him. Or if he asks why I'm avoiding him then I'm happy to discuss it with him and tell him the truth. I'm happy to end it on peaceful terms but yeah I don't really think I want to be friends anymore.

It sounds like you might have a wee bit of a jealousy issue. Not that you are jealous of the guy or your female friends, but you might be a little jealous of the care that you show them and the lack of care that they return. I say this because I have been there. It totally bites when you are a person who gives and gives, and your friends just take and take. But, we continue to to this.

What I've learned from experience: as tough as it might be, sometimes it is better to put a distance between you--ALL of you. And, if you do continue to hang out with A, set some very clear boundaries. I would tell him that you are not his therapist, nor are you his matchmaker. If he has any maturity whatsoever, he will agree.

How inaprorpriate and disrespectful to your fiance to invite a guy you on and off slept with to your engagement party. You are worried about what A does, why he isn't your friend, what friend of yours he is banging and you really should be focused on your fiance and not care about A anymore. Are you truly devoted to spending the rest of your life with your fiance if this dude you have slept with and remain entangled with is high on your mind? You don't need to "end on peaceful terms" with a dramatic goodbye - just devote yourself to your fiance -- A will go away if you stop engaging him and he has tried to go away before. Let him

He sounds awful. You were his doormat. Why would you waste any time with this user?

Lose him!! He was never your friend! You need to be more discerning and establish boundaries.

Look up codependency. It fits you to a t.

A sounds like a stunted manboy. Classic type, that. What he offers you today, at 35, is essentially the same thing he offered at 25: a dash of genuine heart, somewhere in there, but primarily a lot of shallow attention and drama, the kind of stuff that feels super meaningful when you're young but loses its shine as you get older and start swimming in deeper waters.

Most of us have a few friends like this—the ones that never grow up and start falling by the wayside. Growing up doesn't need to be marriage and mortgages, but just maturing past a certain kind of behavior. Not really in his wheelhouse, by the sounds of it, at least not yet or not with you and your circle. He's stuck in a loop, literally and figuratively, and seems to gravitate toward people who will keep him in that loop.

You're one of those people, sadly. Which once worked for you, in ways, gave you something. What was that something? Well, only you can say, but it sounds like you got to experiment with things that feel radical and mature when you're young—transitioning from hooking up to being friends, say—and perhaps a little hit of confidence for being a bit more superior to the other characters in the drama.

Time to let go of all that, I think. In your shoes I'd just let it fade. He's one of these people that kind of lets life happen to him, rather than make any real moves to level up. Tough energy to invest in. Slows you down and twists you around, and I think as we get older we just realize the importance of investing in people who keep us level and level us up.

How inaprorpriate and disrespectful to your fiance to invite a guy you on and off slept with to your engagement party. You are worried about what A does, why he isn't your friend, what friend of yours he is banging and you really should be focused on your fiance and not care about A anymore. Are you truly devoted to spending the rest of your life with your fiance if this dude you have slept with and remain entangled with is high on your mind? You don't need to "end on peaceful terms" with a dramatic goodbye - just devote yourself to your fiance -- A will go away if you stop engaging him and he has tried to go away before. Let him

Well, regarding my fiance in this situation. We actually don't have a rule in our relationship that we are not allowed to associate with people we have previously hooked up with. We had a talk about this when we first began dating two years ago and my fiance said that he did not have an issue with this in and of itself, as long as I was always honest and I was not actually doing anything with other people. I am still friends also with an ex of mine and another FWB and my fiance is friends with some old FWB too. However he's originally from interstate so none of his friends or FWB are actually here, whereas mine are.

Just to add also, I only hooked up with this friend A in 2009-2010. So it has basically been ten years now since anything physical happened. I know from this post it sounds like I'm preoccupied what A is doing but all the drama I mentioned I was kind of dragged into not by choice. I stepped back when he was in a four year relationship with that girl and also when he deleted me for six months I never said a thing. Now he has come back and is contacting me and my gut feeling is that I'm pretty over all of it and I don't really want to be friends. But I have not been chasing this person myself.

Well, regarding my fiance in this situation. We actually don't have a rule in our relationship that we are not allowed to associate with people we have previously hooked up with. We had a talk about this when we first began dating two years ago and my fiance said that he did not have an issue with this in and of itself, as long as I was always honest and I was not actually doing anything with other people. I am still friends also with an ex of mine and another FWB and my fiance is friends with some old FWB too. However he's originally from interstate so none of his friends or FWB are actually here, whereas mine are.

 

Just to add also, I only hooked up with this friend A in 2009-2010. So it has basically been ten years now since anything physical happened. I know from this post it sounds like I'm preoccupied what A is doing but all the drama I mentioned I was kind of dragged into not by choice. I stepped back when he was in a four year relationship with that girl and also when he deleted me for six months I never said a thing. Now he has come back and is contacting me and my gut feeling is that I'm pretty over all of it and I don't really want to be friends. But I have not been chasing this person myself.

It doesn't matter if your fiance is okay with it - you should not be okay with it.

If you stepped back when he dated someone and deleted him, now YOU are with someone and you should do the same.

The bottom line, he is a terrible friend and jerk. I don't understand why you had anything to do with him! Raise the bar!