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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.

I get it, but $5 to change someone's life?

It's funny there was a moment I was at a bus station, somebody asked me for money and I dumped all the coins I had in my wallet in their hand for future bus rides. And some lady comes up to me jokingly like "you handing money out? what about me".

But yeah I think I should just give the money out, I think aside from the guy at the red light that's there almost everyday when it's warm, it's rare I encounter somebody personally. Until I go into the city.

Buy someone new clothes. A sleeping bag. Utensils. A library card or bus pass. If it has to be cash, you don't have to stop at $5. I sometimes give out tens and twenties. Obviously at a place like California your altruism can be spread pretty thin; just ignore the people who are more difficult / less appreciative. Find someone who is appreciative. Get to know them and find out what is holding them back. Maybe you can't help, maybe you can. I've had people tell me I've made their day, their week, their year.

It's that thing though I'm pretty sure I was scammed by this couple at a gas station asking me for "gas money" even though they wanted cash then the lady said "your mother raised a good boy" lmao.

To me this is a gov problem not an individual problem. Yeah if someone was dying in front of me I would try to help them. But now I gotta go to a store and buy em a tent and what not? I guess I am an asshole. Also read up "do you give money to homeless" on reddit. Almost all of the answers are no.

I have to go there and face my fear. See if I do get assaulted, I'm a 6ft buff dude so I don't think so but I'm also not a trained fighter. I just hate this fear, that normal people like living in NYC deal with on a daily basis.

Getting jumped is real though, I've been jumped before by a group.

Might as well just give the $5 though and move on with my life.

Back to women, I have negative traits as demonstrated above, indecisiveness and low self-esteem/caring about what other people think of me too much.

All this stuff is stupid, "I'm a good person because it's what people think you should do" give money to a non-taxed church, politicians, etc... then the individual person not giving a dollar to a homeless person is a bad guy.

There's risk to helping people out.

I've been fucked over plenty times, sometimes to the tune of 5 digits. Once even cost me my home, and I found myself homeless again for a while.

A good friend of mine once gave someone a ride at a gas station, and they led him to a house where another person jumped inside the car with a gun. They held him hostage, tried to force him to do fentanyl at gunpoint, and drove him around to several ATMs so he could empty out his account. They used his vehicle to sell drugs, and held him hostage in a motel room where they were also sex trafficking women. They nearly killed him, and he is lucky to be alive.

I also know others who have been jumped around here and had the shit beaten out of them. For reference, I live in a city frequently cited as a "murder capital" of the US. You have to be way more careful out here than in downtown San Francisco. As far as NYC, I imagine it's a mixed bag depending on your area. I'm not suggesting naively approaching strangers, I hope it doesn't come across that way.

You aren't an asshole if you don't buy someone a tent, I was suggesting ways to help that have more tangible impact than handing someone a $5 bill which probably just goes towards an addiction. I don't hang around Reddit, so I can't speak for the general callousness of the community, but what I'm suggesting is to go beyond the average, to do more than most would, in reverence of the fact that we're all floating on this lonely space rock together.

As far as women, all I can say is that my girlfriend would be fine with any of those traits, as long as I still maintained a level of compassion.

There is also the thought of too many people to help. Like right now there are thousands/millions of people starving is it my fault? Should I empty all of what I have to help them because I'm guilty if I don't. That's what I'm wrestling with granted what we're talking about is not the same thing. Handing somebody $5 and moving on is not that but yeah idk. I guess as a person that keeps giving shit out eg. $100K to my own family, it gets old.

But I will go out there, I'll see what happens. I need to face my fears.

I hear you. I've had ungrateful family members drive me broke. Compassion is doing the right thing, even when it's scary, or it hurts, or no one is watching, or when people around you misunderstand and demonize you, or they are just plain ungrateful and leave you holding the bag. I admire your willingness to continue grappling with it and finding your own answer.

Regarding women again, are you meeting enough of them? What's the scene like where you live? I don't know what it's like in NYC, but the social/dating scene in my current city just doesn't exist, and I'm watching some of my friends grapple with seriously heartbreaking loneliness.

I don't know what to tell them. I'm dating my high school sweetheart again, but we were broken up for several years, and many of the experiences I had with women during that time were quite traumatic. The rest of them were just not a good fit. I had completely given up on dating altogether, at least for a period of time, and only then did the love of my life find her way back to me. Despite years of extreme loneliness in new cities, I still consider myself lucky and wish I had some actionable advice I could tease from the situation. I've even experimented with building dating apps because this epidemic just scares the shit out of me.

I'm not in NYC sorry to give that impression. I was mentioning NYC as far as being densely populated, I'm in the midwest. Honestly I don't meet much women outside of work or the occasional girl I run into at a gym. I know the cliche saying "go join a club" meet girls that way. I could see that but it's also possible I like being alone too but yeah it just bothers me that my self-deemed value is whether or not I get laid.

The other problem too today is the fakeness of social media, filters on faces, photos looking like peopel go to beaches all the time/live extravagant lives.

Bars it's like a self-control issue, use drinking for courage then you get too f'd up.

In the midwest but we have a small "city" with "skyscrapers" that I wanted to go into and do photography at.

> I buy people lunch and sit on the curb eating with them and attempting to understand them.

I clearly don't have the same people on the street as you do. You should not be just sitting down and having lunch with people who are having daily psychotic breaks or are otherwise aggressive. You can't have a conversation with someone who is constantly riding the line of ODing. I have a regular I see who runs around in the road screaming at cars and people.

The very incomplete "down on their luck" view of homelessness is killing progress in my city.

I have lived in many metropolitan areas and have seen the gamut of homelessness. As I mentioned in a downline comment, the trick is to ignore the people who are not in a position to receive help, and actively seek those who are in such a position. I am not suggesting walking up to random homeless folk in San Francisco who are tweaking out and hanging out with them. I am not suggesting to risk your safety by approaching the first person you see. You live in your area; study it, pay attention, and over time you'll start seeing some familiar faces. This has worked for me in New Orleans, it worked for me in Texas and worked for me in California.

So I'm willing to bet that my understanding of homelessness is more nuanced/holistic than even yours. I have been homeless. Have you?

What progress do you feel is being hindered by a collective display of compassion?

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.

Yeah that's the cliche saying, let them chase you or don't put on a pedestal. Idk not sure if it's because I was raised by women that I need their approval (no male figure). But I know other people who were in the same situation and aren't like me so it must be a personal choice/way you decide to overcome it.

The basic problem with this is that the ones that are trying too hard are doing so because the standard approach failed.

Maybe you get lucky, but it's not a general solution.

What is the standard approach?

I find that being genuine and vulnerable and having no hidden agenda works wonders.

For me it was the other way around. For many years I tried hard and I was wondering why it did not work.

Oh you haven't gone anywhere near far enough with this.

You'll get laid the most when you adamantly pretend like you're not interested in getting laid. You actively have to act like you are "too good" for them. Play "hard to get". Learn what "negging" means.

Never, ever, show desperation for anything ever for any reason. It is the ultimate ick. Buddhists will even tell you that desire is ontologically/spiritually evil and icky.

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.

Yeah it's funny I'll sound like I'm virtue signaling here, I donate. Food groups, NHA, stuff like that. Where I live there's usually a person at a red light waiting to "ambush" you. Same at a grocery store, soon as you exit the door solicitors going "excuse me sir".

But yeah it would be easy to just have a $5 to hand out. It's just you know how many people are there and will it stop there kind of thing. Yeah I sound like an asshole I get it. I also have sent over $100K to my own family in support and I'm -$80K in debt so it's not like I'm hoarding my money or something.

It just annoys me. But sure it'll be easier to just say "here you go" and hand out cash.

You don't sound like an asshole because you aren't saying bad things about the people who have the least.

It's up to you, you can just, to yourself, write down the words you'll use to write down that you'll ignore them to become more comfortable with your boundaries.

Personally I don't think handing out cash is helpful so it's not about charity it's my advice to pre-plan how you'll respond to be more comfortable than you are in reaction to these situations.

It is a quick escape though to be like "here you go" and move on but also opens you up to "that's it?" I've had that happen even when I said "I don't have cash" well I have Venmo I'm like alright... yeah I don't want to have this mindset but also can't be naive too kumbaya.

In my experience a few times people will ask for money if they see you giving someone else something, but not that often, and you can shrug through it and say that was your last dollar or something. Keep the interactions short and easy and try to carry the loose bills outside of your wallet so no one can actually see how much you have inside it?

Exactly one time after I did this, a guy asked me to send something to his venmo since I really only had a dollar. Probably my strangest interaction.

Yeah I'll probably be smart and just empty my wallet except ID and some loose cash. I just don't like it the idea someone coming up to you asking you for money and you're expected to just do it, give it to them. It's funny too as soon as they get what they want or don't get what they want, they're like f you and move on. Ahh well I just wish I didn't care. I'm too soft/care what other people think of me.

It's like points on a website "oh no I got downvoted", there's a thing as being you/not being a conformist

I think I purposefully need to get into a fight you know overcome it, like expect anyone who comes up to me to fight me

I'm gonna stop ranting but it's not like it's hard to get laid, it's just my standards are high like she's gotta be a dime or fit at least. So that means I also have to be fit/good looking which I haven't cared much before as far as good haircut/good clothes. I at least am lucky with my genetics for fitness but I also have not been as cut as I could be. But ultimately I know it's my mind that's f'd.

     a guy asked me to send something to his venmo

Ah, the mark of a true professional beggar. ;)

You have the right but not the obligation to give. The person asking has heard a lot more no's than you could stomache, so one more won't kill them.