Somewhat a tangent response

I have a fear of crowds and bums. Not where I'm paralyzed/medicated but one thing I'm trying to do is go downtown and do street photography. I wonder how do I say no to a stranger asking me for money. Or fear of getting robbed. It's not like my camera gear is that expensive but yeah. This would push me to get out there more as I've lived in the same place for 10 yrs and I haven't really explored/gone around much. Other than when I did Uber Eats, I would go all over the place. I would get wasted/drink at bars but end up with nothing end of the day, temporary day-long friends.

Funny I was at the gym yesterday, guy said hello to me, as a guy that keeps to himself usually (unless around friends) I gave him a bad look (not on purpose) and then I responded. I'll say hello next time I see him.

Yeah for me it's just fear and lack of exposure. I do make a lot of "work friends" go on walks. But yeah real friends I think I have 4 or 5 lifelong real friends. Women nothing, haven't been laid in like 12 years pretty said to say. Unfortunately it's something I value myself like "I'm a loser by not getting laid". Even though rest of my life is good, 2BR apt, sporty car, six-fig job, but yeah. It's my social awkardness, but I lift/improve myself, cutting down on weight I want abs. Idk I'm not going after women anymore either just trying to live life now, do shit, get out of debt, get out of 9-5, mental freedom.

It's funny if it's guys I'm very "charismatic" like I can be "everyone's friend" which doesn't work out due to conflicting interest. To that end it's really about taking an active interest in the other person, engaging them, asking them questions and remembering.

My thing with women is I don't get along with them like a guy (where I don't want anything from them physically). If they're not attractive then it's easier to talk to them but yeah, I guess that comes from a desperation mindset.

Hear me out. Its not just social awkwardness. You're experiencing class boundaries and do not seem to have the right mentality to bridge the gap.

First, you call homeless people bums, which sets the stage for how you see and treat them.

I'm an excellent engineer, but I was abused and impoverished as a child, homeless as a teenager. During my 20s, I started a few companies but my savings have been continually depleted taking care of family members. I don't have a sports car or a big bank account, or nice cameras. When I see a stranger or homeless person, I smile and wave. I keep cash on me so that I always have some to give out. I buy people lunch and sit on the curb eating with them and attempting to understand them. I learn the names of my local homeless folk and ingratiate myself in the community. I've moved to a few cities so I've had the opportunity to do this a few times.

I don't do this because I lack social anxiety; I sometimes have extreme agoraphobia, to the point that I have to hype myself up for hours just to go to the grocery store, and I have to wear noise-cancelling headphones to reduce the amount of stimulation. I have PTSD. I'm an extreme introvert. A hermit at times.

But what saves me is the philosophical understanding that I have a duty to the social contract. That empathy and direct aid are nonnegotiable parts of being human. I've been homeless and I know what it's like to be truly hopeless and live a life of uncertainty, fear and hunger.

You need to bridge that gap. Class-induced anxiety is real and I acknowledge that it's probably difficult, but it's not an excuse. You sound like you're in a position to change someone's life. Taking those steps might change your own life.

What I found after many years, is that women (people in general, really) are not attracted to people who try too hard to get attention from them. Going through great lengths tends to result in being labeled as desperate or creepy. Try just to be friendly and talk "with" them and not "to" them, almost as if you are one of them. By doing that often enough, it will feel less awkward. Practice makes perfect. And then one day you feel a click with someone. Just my few cents.

I found it uncomfortable as a kid when I saw how my parents handled begging: ignoring it. I remember one time my father saying "that's ok". And I either say "no, sorry" or ignore.

I've heard of kids from cities being given money so they always have something to give a mugger instead of looking like you're holding out, I don't go that far but I remember it to keep perspective.

I recently made an effort to carry cash with me so I can leave tips in cash, still working on that. Would you be open to keeping singles on you to give? You can even give max of one per excursion and then decline or ignore the rest or any combination but maybe having that as a plan can help you feel comfortable. Yes you're training yourself and it's because you deserve the benefits of training.

As for non-bums hello is good, also fist bumps and nodding upwards; that stuff is cool AF and make people so damn happy.