How should I handle a friend who is judgemental and insensitive?

I wouldn’t consider someone that constantly criticized me to be a friend. If he really is miserable all the time, it could be that he doesn’t want to hear about the good things you have going on. Do you really want to salvage this friendship? If you want to salvage it, I’d give him a day or two and then call if he hasn’t called yet and talk about what happened. If you don’t like the constant criticism, tell him that and tell him that it needs to stop if he wants to keep your friendship.

The relationship seems a bit toxic. Shit doesn’t need to be this hard. It sounds like you overreacted a bit and I could understand if he didn’t answer your call or is unwilling to carry on.

I wouldn’t want to listen to that either.Maybe you should give it a few days to cool down then call and maybe you can talk it out. Good luck and enjoy your break! :)

@johnpowell you really think I over reacted? This guy had been caught bashing me behind my back to my ex and makes sly suble comments about me not being too bright but you still think I am the one who over reacted? He didn’t even call to apologize for upsetting me. Hmmm.. well thanks for that opinion.

I’m curious, have you paid him back when you have borrowed money from him? Do you only call him when you have a problem? Maybe he is tired of you using him as a sounding board and not being a real friend to him.

Thanks @Seaofclouds @lucillelucillelucille . It’s hard for me to listen to him constantly bash everything I do. He told me he doesn’t bash me when I tell him about things he deems positive. I feel it’s not his call to judge what is good or bad based on his own ideas. He doesn’t like Gay ppl and that is why he was disgusted that I wanted to go to the parade. He is very narrow minded and openly admits to not liking “certain” ppl. A friend should be there for you even if they don’t necessarily live their lives like you do or agree with your ideas.

@Akua I’d say that we are only getting your side of the story here. Before you get angry at me, please hear me. Stephen Covey, in his book The 7 Habits of Highly Effective People, has some basic rules. One of them is “Seek first to understand.” I pointed this out to someone here, and then realized that this is what I needed to do. I’ve been taking my own advice since then. You present a very one-sided view of the story, but I’ll wager that there is a lot more to it, and that you know more than you’re telling. So stop, take a close look and be honest with yourself.
You’ve known him for this long and at this point he started acting differently. I won’t belabor the points that @chyna brought up, but you know the answers to this and other questions.
Doesn’t like gay people? Kinda harsh. If that is his only objection, then maybe you and he need to come to a parting of the ways. But my first thought was that he feels that you are wasting resources better spent on other things. Is there any way the two of you can talk about this and get to the bottom of it without rancor, recriminations or things getting ugly? Do you feel that the friendship is worth saving?

@chyna because of serious financial hardships I have not yet been able to pay him back. He offered me the money and never asked for it back to his credit. And no I don’t only call him when I have a problem. I had been calling him all weekend to make sure he was ok because I know he was stressed about having to move and look for a better job. I was in a great mood when I just happened to mention I was going out later. Sometimes I will call him and just to make him laugh I will call and share a funny story about something I saw or heard. And when he was depressed about not being able to find a teaching position, I was his cheerleader that told him he was the greatest and he would get a good offer soon.

If you want to continue the so-called friendship, listen and don’t be judgmental or insensitive. You have a different definition of friend than I do.

@Akua -I agree with you.He really does not sound like a good friend and you might be better off without him.

It really depends. If you are still borrowing money from this person than you invite this person to be entitled to critize you. Especially if you borrowed and never paid them back.

Maybe he is alone because he has had a crush on you and is waiting for you to wake up and stop dating people that never seem to be there to help you out.
Or maybe they are simply feeling used and realize that you intend to use them as a crutch for as long as possible and will never change.
Bottom, line. If you never want to be critized than don’t borrow money from this person and don’t give them a bunch of stuff to critize.
Example, I hate it when people whine about not having money and can’t pay the rent, but they can somehow afford a boob job or a flashy expensive sports car. However, now they have used all their saving and whine about how some people have it so easy in the world and they have to live pay check by pay check.
I knew a lady like that once. Didn’t have enough money to properly clothe her baby but she was able to borrow money from her parents to get a boob job. Then she didn’t understand why the rental office was giving her a hard time about paying her rent when she just got out of surgery.
(She didn’t need big boobs. She already was one.)
Point is some people invite critizism.

@Pandora I borrowed the money once from him and never again and he knows I don’t spend money or make a habit of asking/ borrowing from anyone. Way off base on that one. I don’t even buy toothpaste (i’d rather save the money and use baking soda) and I don’t even own a vehicle anymore. I agree he may have a crush on me though because he did insinuate that when he met me he was disappointed that he always ends up in “friendville” with women and that he wasn’t happy when I came back to NYC. Thanks for the feedback though and I’m grateful to everyone that replied. I know he is under a great deal of stress this last 2 years and has had some personal issues and so I will give him time to cool down and I will contact him to make sure he is ok.