How do I deal with this friend?

[xplorer]

Before I left to Australia from UK, I use to spend most my weekends with a close friend, we'd get completely drunk each weekend, until I realized I was completely depressed by the monotony of my life, going to work 9-5 in a crappy admin job unrelated to my degree, and then getting drunk on the weekend and looking to get laid. Then the same cycle all over again, thats when I decided to move to Australia a pursue my dreams, however my friend continues to do the same thing, he has two degrees, in media and history, yet has only worked sales jobs, we're both 27. And have graduated university for a years now.

He doesn't really consistently work, he'll take up these sales jobs now, and quit them after a few weeks, saying he hated the boss. He lives at home with his mother, who is a widow. He doesn't seem to have any real direction in life, when I ask what he wants to do, he'll come up with something vague saying I'm looking a career change, something out of the office, but never really follows through.

He distorts things, from what really happened, he fell out with one of his best friends a few year ago, and use to tell me how arrogant he is. Yet a few years after I mentioned it in a conversation how they've made now from when they fell out. But he denied it happened, and said they never fell out at all.

He'll boast about how much he can drink, and boasts about getting laid, saying he lost his virginity at 12 and has slept with over 70 women, and is amazing bed. He use to constantly try and preach to me when I was drunk and depressed, saying I shouldn't bear grudges against school bullies, and would try and help get me laid, he said seen himself as an older brother figure to me, even tho I'm a few months older than him.

Looking back on it, his preaching gets on my nerves considering he doesn't really have any direction within his own life other that to get drunk each weekend. He likes to make out he is a manipulator, and try pull of this whole, Charlie Sheen like, womanizing, bastard image, and will brag about how he his sleeping with other women whilst he his dating a girl who thinks she is in a relationship with him. He validates himself through drinking and getting laid, and he'll sleep with really ugly women, and hang out at slutty bars. He preaches that I shouldn't care how good looking the girl is if I wanna get laid.

I'll be going back to UK next year to visit for my sisters wedding, even tho I'd like to see him, I know he won't have changed at all, and will want to invite me out to drunk with him, and he'll be preaching and bragging again.

[DevilsAdvocate]

I had a professor once ask me how'd I feel if one of those types of friends put me down as a reference on a job application. How would you feel if they represented you in that aspect? I know I would be ashamed and humiliated. There would be no way I would walk into that company and hand them my resume knowing they still have a bad taste in their mouths from him. We all have at least that one friend, generally from high school, who never seemed to grow up. My "Peter Pan" was a friend from my greek society. Drunk every night, sober (almost) enough to go to classes, drunk every night. Guess what... they are still doing that... at the same college too. Those types of people never move up in the world. If you feel that you are better than the life style that he is living, dont get sucked into it. From the sounds of it, you arent asking what to do about this friend, but more whether you should feel guilty about how passionately you are despising him lately. Personally myself, I say GOOD FOR YOU! Shed the dead weight on your social platter and get friends closer to your maturity pallet. It will benefit you in the long run.

[DevilsAdvocate]

Forgot to ask: Do you have any memories that start off with this?

"Ya know... if Bob didnt drag me to that strip club last night, I probably wouldnt have missed that study group." Or something along those lines that might be more appropriate to your age? If I had to bet there are stories about how he had his hand in your failures and also how you had to carry his weight at times. When was the last time he did something for you? No strings attached, out of the kindness of his heart...?

[xplorer]

From the sounds of it, you arent asking what to do about this friend, but more whether you should feel guilty about how passionately you are despising him lately.

Well to be honest I'm very introverted and have few friends, and he is only one of the few close ones I have back in England, if I met a girl in Oz, and decided to take for a visit to England she'd probably be interested in the friends I have back at home, I wouldn't want to have to say I don't really have any friends in England at all. On the other hand he was someone to go out with on nights out and enjoy myself for abit, so even when I do go back to England next year to visit I would like to think I can enjoy myself for abit while out there, and catch up with him.

Forgot to ask: Do you have any memories that start off with this?

"Ya know... if Bob didnt drag me to that strip club last night, I probably wouldnt have missed that study group." Or something along those lines that might be more appropriate to your age? If I had to bet there are stories about how he had his hand in your failures and also how you had to carry his weight at times. When was the last time he did something for you? No strings attached, out of the kindness of his heart...?

We never really met up with each other again after high school, until our final year in uni, so he has never really had his hand in any failures. He did try to help me when I was down and depressed, and tried to help me get laid, I would like to think it was out of kindness, but it could of been ego driven, as he like to boast about getting laid.

But practically every meeting with was going out and getting drunk, he asked me if I thought he was fat, I tried to be honest with, and you do have abit weight, if you didn't drink so much you'd be in pretty good shape.

But he denied that was the reason, and said its because he eats a lot of junk, and that he would like to have a social so that is why he drinks. He use to heavily criticize another guy I was friends with, who did not drink, and say what is the point of going out to clubs each week if you don't even drink and get laid.

The thing that irritates me is just because that he has had more experience with girls, and has lived more of the drinking lifestyle, it makes him an older brother figure. And he preaches that I should be living life to the max, and embracing my wild side. While some of that is true, and I wish I had been more outgoing and wilder when I was younger, and enjoyed life abit more, but shyness was an obstacle. I would like to think I have more balance, and a steady income, and my own house one day.

I would like to go back to England and maybe give some of advice my own to him, and help him grow up, but the thing is he needs to be right, and doesn't really acknowledge his own problems, such as his weight, drinking and no real clear direction in life. I think if I did try to give him advice, he would just tell why I'm wrong. I've listened to his advice constructively before, and it did help me out with girls abit, some of the stuff he said about my own insecurities was true I have to say. But I took it in and worked on it, if I gave advice on his own issues, I get the feeling he probably wouldn't listen, and give pseudo insights into why he doesn't need to improve.

I feel if I can't help him out as well, I won't feel as though we are level with each other, and it will just be him seeing me as this younger brother figure, looking for his approval, and advice.

[TS]

I think it is almost impossible to change your friend, which does not mean that you should stop your interaction with him. I have known completely different people who were nonetheless good friends. And, as you mentioned, you have few friends and you don't want your girlfriend to discover this.
Besides, your visit to England will be short and you don't have to spend every evening with him. Try to concentrate on the positive events that you both had together, which make you both laugh, and when he starts preaching try to turn it into a joke or answer sarcastically like "Oh, you have achieved so much in life, become a millionaire, you are the one to teach me." Probably after this he would feel inferiority complex and stop treating you like an elder brother.
Your friend's behaviour can be explained by the feeling of depression and frustration. Having 2 degrees, he has not achieved much in life and, understanding this, uses the mask of "Kasanova" and forgets about his problems only with the help of wine and women. I think he is not the one who is not self-critical, but the one who is frustrated and unable to manage his own life, and he deserves pity.