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How to deal with strange, subtle rude comments?

The best way to describe my brother-in-law is that he has a chip on his shoulder. He makes weird statements that I find incredibly rude and annoying but the stuff he says is so strange I'm not even sure how to call him out. Here's an example. I bought a new car. He said, "That's what all middle aged people do when they start to panic that they're getting old." For the record, it's not exactly a flashy sports car but I didn't say anything because I wasn't sure how to respond. Another day he saw me loading my kayak onto the car and he said, "Your life is even more boring that I thought. You think floating in a plastic boat is fun." If he were joking or just having fun, I'd be fine. But he says these things completely serious. He's not really a fun or funny person. Instead, it's mean spirited. But comments like this often drive me crazy for days as I'm thinking about what he meant or what I should have said for a comeback. Should I ignore his comments or speak up? And what would I even say?

I lost my job and I'm having trouble staying mentally strong. What can I do?

I was unexpectedly let go from my job three months ago. I'd worked there for about 10 years and was blindsided. I thought I'd be able to find a new job pretty fast but it's taking a lot longer than I imagined. I'm a professional with a lot of good experience. I've applied for a lot of jobs and only had a few interviews but no luck. I'm discouraged and starting to feel panicked as I need to get a job soon. I've been meditating every day, exercising, and trying to take care of myself but I still feel awful. I have an interview next week for a job I don't even really want but I'm starting to feel a little desperate. How can I stay mentally strong when I'm out of work and can't get a new job?

What's the best treatment for social anxiety?

The older I get, the more I realize how social anxiety has affected my life. I created a life that feels safe to me but now I realize I missed out on a lot of opportunities. I want to work on fixing my social anxiety so I can build a bigger life but that would require a lot more social interaction. What's the best way to overcome social anxiety?

Is there anything I can do for my adult child who is an alcoholic?

My son is clearly an alcoholic and I'm slowly realizing just how bad his drinking has become since his divorce two years ago. When he's drinking a lot he sometimes calls to tell me how depressed and lonely he is. When he is sober he acts like nothing happened and says he is OK. Is there anything I should be doing to help him? Am I providing emotional support when I talk to him even though he doesn't seem to remember it the next day?

Taking medication for my depression feels like a crutch. Should I be strong enough to handle this without pills?

I've had depression for quite a while and my doctor is aware. He keeps telling me I should take medication and that medication might help me. But I can't shake the feeling that medication is just a crutch. I don't want to go for the easy fix but it is tempting sometimes to just do it. Is taking medication a crutch I shouldn't need?