First: HUGE kudos for posting this. That took courage.

Next, this is going to be a bit long. Apologies to all for that. Like Mark Twain said: if I'd had more time, I'd have written a shorter letter.

My name's Chris. I have a handful of close friends, and an amazing wife. And every single night I fall asleep filled with overwhelming gratitude for that. Because I know I could just as easily be completely alone. My friends have done the lion's share of the work staying in touch. I have a more balanced relationship with my wife, but that's what love has done for me: I want to make that woman happy more than anything, and that just washes away any barriers between what I want and what I actually do.

Like I said: lucky.

All this is to say: I don't think you and I are so different. I have trouble feeling emotionally connected. For me, it takes work, and some conscious effort, even with friends I've known for decades.

Okay, so. About not being able to cry. It sounds like you spend a lot of time and energy trying NOT to feel things. Trying not to feel lonely, not to feel discouraged, etc. The crazy thing about emotions is that you can't pick and choose what you suppress and what you let out. It's all or nothing. So clamping down on all the negative stuff is going to keep all the good feelings down too. So it makes sense that you're numb to good stuff like camaraderie, friendship, emotional support, etc.

And keeping a lid on all that emotion is exhausting. No wonder you sound tired.

Letting in all the good in life starts by opening the door to all the shitty emotions, too. That can be a bumpy ride. You're already seeing a therapist, and that's awesome. (Me too!) Don't give up on that. Medication can help. If your therapist suggests it, do it.

(But: SELF-medication is worthless, and masks one problem with another. I've avoided that trap, but I've seen it up close and personal.
Trust me. Don't go there. Like the old joke goes: "...now you have two problems.")

But here's the payoff: as overwhelming as all your negative emotions feel now, that's how big all the good stuff is going to be. HUGE.

If the "talk to a stranger every day" exercise isn't working, then change it up. Therapists say talking to strangers is easier because it's low-risk. Odds are you won't see that person again, so it's no big deal if the conversation is uninspiring. But it sounds like that's part of what makes it discouraging for you: you want to make new friends, and you feel like talking to strangers isn't going to help you establish those kinds of friendships.

So change it up. My therapist told me to keep a "gratitude journal," where every day I write down something that makes me happy. I thought that was dumb, so I did it my own way. Instead of writing it down, I took a photo. After a few weeks, I was constantly looking around for cool stuff to take pictures of. And habitually looking for the good in my day was exactly what the journal was meant to achieve.

Point being: the talking to strangers thing is a suggestion. If it's not working, change the rules so they work for you.

My suggestion: join a group that does something that's exciting to you, but new. For me, it was Krav Maga class. I was bullied as a kid, and so confrontation was REALLY uncomfortable, physical confrontation doubly so. Krav shook me out of my usual habits, and let me establish casual friendships with the guys in the class over time. It was a different kind of low-stakes social interaction:
instead of being sure I'd never see someone again, I was sure I'd see them again next time, so I didn't get self-conscious, and I didn't think too much about evaluating how it went. It was just a bunch of guys and girls having fun together. And being in a class gave me a certain comfort level: I knew that if I didn't feel like talking that night, I could keep the small talk to a minimum and nobody would mind.

But don't just take my suggestions either. Figure out what works for you.

Let's talk documentation.

Check out a book called, "How to Talk so Kids will Listen, and Listen so Kids will Talk." It pretends to be a book about skills for raising kids, but it's actually about really listening and connecting with people. It is AWESOME.

My other go-to book is called "Practical Programming for Strength Training". It's about weight training (y'know, with barbells &
stuff), but the principles are incredibly broadly applicable. It's about finding what works and what doesn't in pursuit of any goal.
(Plus, physical training has gotten me through the toughest times in my life. There's nothing like getting physically stronger to make me feel emotionally stronger.)

And I'm currently reading a book called "The Inner Game of Tennis". This one pretends to be about how to learn tennis technique, but it's actually about letting go of judging yourself, which is a skill worth having.

And finally, I'll share something that I learned in my years trying to reconnect. There's a really bad old song that talks about "if you want me to be closer to you, get closer to me... if you want me to love only you, love only me." I'm not a fan of the song, but there is some serious wisdom in it. Connection works the opposite of how I thought it did. I thought that people would be interested in me and my life if I made myself and my life interesting. But it's the opposite: you make friends by being interested in THEM. You draw energy and support from a friendship or romance by GIVING to it. You best improve your own life by working to improve the lives of the people around you. It's all inside out.

Fight on,

-Chris