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Friendship dilemma: How to break up with a friend who's also your friends' mate?
I know this post is a bit long, but I'm really looking for advice because I can't talk to it with most of my friends 
Last year, I met this guy at school, and we became friends. Wherever I was, he was also there. I didn't mind it because it's normal to have friends at school after all, plus, I was studying much of the time anyway (even though he would often convince me to do something else, because I didn't know what "discipline and organisation" meant till recently ). Time passed and all the friends I made at school eventually met him (and vice-versa), and we soon had the same friends.
It was a weird situation: at the same time he was this very nice guy who would take me anywhere in the city, lend me money whenever I needed (he was even willing to lend me 1000 U$ dollar so I could go to Russia) and do all the stuff friends do (I was extremely depressed back in that time and he would often help me out), I couldn't stand being beside him for much time. He was always complaining about things, criticising people (specially me), saying that "we were bothering people" (which made me feel paranoid for a while, thinking that I was indeed annoying everyone I talked to),..., and after some time I started to dislike more and more others aspects about him, and even his humour became annoying and childish to me (which made me feel afraid of being that way too, since I'm usually joking and stuff).
When he got a girlfriend I managed to keep some distance, started to enjoy my other friends more and stuff, but as soon as she broke up with him, he realised that I was more distant and started to ask me if I had stopped talking to him because he's boring (to which I replied that I was just spending too much time with my studies, which was true). A bit after that, he started to visit me more often, which led to a partial loss of privacy (whenever I asked a girl out while I was at home, he would know it, because he was there)... he even started to look for me in places in which I could be whenever I wasn't home (thank God I haven't got a mobile phone).
Friday we argued he noticed how fed up I was. Monday, he called me three times and sent me a couple of e-mails (Sunday he was working somewhere all day long, mind you) and Monday I couldn't answer his calls (nor answer his e-mails) because I was shaking in bed because of a fever, which made him believe I was avoiding him, as I was expecting 
I would consider breaking up with him, but, as I said, most of my mates hang out with him too (my sister's boyfriend, some girl I've got a wonderful feeling for, other good friends I have,...) - I don't want to lose it all. Plus, I know the guy really well: if I talk openly to him he'll get extremely hurt and I just can't be that harsh on people, he's a nice guy deep inside.
Someone got an idea of what I could do? I feel selfish and shallow 
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