Stuck, Lacking Engagement in Conversation

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I'm at a complete loss. I don't know how to talk to people. I'm not anxious, nervous, afraid, fearful, etc. I just don't know how.

I'm in my mid-thirties. I cashier between college classes(biochemistry) and sleep. Two to three hundred customers per day. After twenty months I've gotten decent(not great) at the basic "How's it going?" two sentence interaction. I've gotten ok at eye contact by cultivating a strong interest in eye color, though I'm concerned I'm overdoing it.

If I try to talk to someone, at work, school, volunteering, groups, if I really try, I can make it last two or three exchanges that feel forced. If I don't really try hard, be myself, just let it happen naturally, etc., nothing happens at all. I just don't engage at all with other people. Not at all, which has left me isolated my whole adult life. My last friend was my cousin when I was eight. My family has given up trying and I don't blame them.

I'm at a loss as to what to do, where to start, what to try. These days I'm trying to figure out how to introduce my name into a conversation. I know it is important because that's how you find out the other persons name but right now it just doesn't make any sense to me. I've been working on these tiny pieces of the problem because with enough time(measured in months), practice, and brute force, I can come up with something that kinda works sometimes.Maybe in another twenty years I can make someone feel uncomfortable for four exchanges instead of three.

And sometimes, once in a while, I'll overhear two other people talking. And you can tell they are engaged in the conversation, and even though it doesn't even rank as more than a way to pass the time between two people with nothing better to do than talk, it's like being shown the sun after wandering in pitch dark for years. I don't know how they do that. Talk for five or ten minutes at a time. It's like witnessing a miracle you will never know in your own life.

I'm at a loss as to what to do, where to start, what to try. I've considered medical means to make myself mute so people would stop expecting me to be able to talk but there is no reasonably safe way to do that. I just don't engage with people verbally at all even though I want to. There are people out there that I am genuinely interested in, want to know. Just don't know how. Wondering if anyone else has overcome this barrier or has any thoughts on how to.

I used to be like this for years and years of my life, I wasn't happy about it either, I strenuously created ways to change it, and now I'm not. So just to say, yes, with application you can improve on this and overcome this way of being if it's not making you happy.

In your cashier work, just some initial eye contact and an opening greeting of "How're you doing?" hello, etc should be fine. That sounds like what you're already doing now, and generally speaking that's all you really need to do. I don't think most people expect or hope for a fuller conversation at the check out unless it arises naturally out of perhaps some very surprising item, like one time I was buying a really brand new type of ladies razor that had only just come out, and the check out woman said "Oh I've seen the commercials, do you think this will be good?" and we chatted from there.

But other than that, just a neutral-to-politely friendly facial expression and a basic greeting is fine, I think, for your work. As a customer that's all I need to feel happy shopping there.

In social situations, starting one is tricky but if you can find something to ask them about, because one good trick is to make it about the other person. One scenario might be that someone you'd like to talk to at a friendly gathering has an unusual looking beverage in their hand, and you might ask "Oh that looks delicious, what is that?" They answer and you say "I think I'll go and get one too -- I'm Mary by the way." They will give their name and then you can follow that with "Do you know many people here? I don't really know anyone except nodding acquaintance."

That's just an example of how you can open an interaction. Then you can keep things going by starting to ask the person about themselves. People are always happy to talk about themselves, so anything where you can ask someone a few friendly but non-intrusive questions about themselves or something they're doing, wearing, carrying, holding, talking about already, will get them doing the talking, and you can listen, and take inspiration from things they say to then contribute yourself, such as they mention they were watching Game of Thrones last night and you say "Oh you like Game of Thrones? I love it too!" (if you do, of course). Then you've found something in common.

Listen to the person fully without trying to think about what you want to say next, because if you really pay attention to what the other person is talking about, it will usually happen that you hear something you have in common with them, or something they've done that someone you know does too, etc. And you can "bat that back" over to them. It nearly always happens that as long as you know how to keep your questions coming at the other person, they will feel like they had a good conversation with you even if you didn't wind up doing much of the talking. Your being a good listener can often make the other person feel like you're good to chat with even if you didn't actually say much yourself.

But often you do get a chance to talk reciprocally if you make sure to pick up on anything you can say something about too, if anything you connect with comes up in their response.

Thank you for your response.

I wish it were easy to just keeping the questions coming. On a good day it can take minutes to think of a first question. And when I listen to people answer I expend so much effort just trying to listen I can't work on more questions to ask. It doesn't come naturally, not at all and none of it.

I feel like I stopped developing socially around seven or eight years old. I think I've picked up enough tricks to pass as normal if no one talks to me or only asks basic questions. I can tell you directions to find a certain street. If you ask me how my day's been I can answer "ok" or "fine" automatically without thinking. If you ask me how my weekend was, or if I have any big plans for the evening or if I'm from around here, the my mind locks up because I don't know how to respond because I don't understand exactly what you're asking and want to know or if I'm supposed ask something back. I don't know if this is a generic question or if you want details or how much detail or you just want me to mirror the question back to you because you have something you want to share on the same topic, and oh, you've walked away because I gave you a terse one word answer while I was trying to figure out what to do.

Naturally is not a description applicable to any part of any face to face interaction I have with any other human being, even with family members. I wish I were different because once you start measuring you loneliness in decades it starts to become depressing.

I used to have the same issue. Especially with girls. The problem was that I didn't care about the conversation itself, just "bonding" with whoever I was attempting to talk to, so the conversation would die because I was trying to create "small talk" but didn't care about the small talk, just the person, so it didn't go anywhere.

BirdInFlights advice was golden. People really like to talk about themselves, what they like, what they're doing, etc about themselves, and that's a great way to make a long conversation with little effort. Here's some other things to keep in mind;

If your not sure how much information somebody wants to hear after they ask super meaningless filler questions like "how was the weekend" or "hows it going?" just reply however you like. Generally if you reply as if whatever your saying is socially acceptable, regardless of whether or not it was acceptable, people just take it, and assume what your doing is okay. If you reply with something super wrong, and people give you weird looks, just own up to the weirdness and don't cower, apologize (Unless you were rude), or discount your weirdness, because the more confidence you have in your weirdness, the more confidence others will have in your weirdness. People like confident weird people.

What I personally do in terms of small talk, is I ask people questions about themselves, but I ALSO single out the questions or topics I personally am interested in. This way, the OTHER person can talk about themselves, and I can stay engaged because we're talking about something we're both interested in.
For example, I'm a musician, and I really like to play the piano. I ask people general questions about themselves as a means of "screening for things I like" and as soon as they mention music, improv, or piano, I get excited and begin asking about their piano life. Eventually the focus transitions from the other persons piano life to just playing piano in general, and the "natural" conversation begins.
Basically, nothing is going to happen naturally unless you want it to, so instead of pretending to care about things you dont, just ask about the things you do. This is why my grandparents always seem interested in whatever I have to say, because although they could care less about what I wrote on the piano last week, they're really interested in ME, my life, and how I'm doing.

On that last note, it also helps to care about, or love others as individuals. That way, although you may not care about your nieces new barbie toy, you care about her and how shes doing, so she could go on for an hour about her new barbie dolls, and you'd enjoy the conversation, (or her presence really) until you needed to get going.

Oh and confidence in yourself, regardless of whether you have any social skills, accounts for about 60 to 80% of your social skills, so if you just do what you do socially, and decide it's okay or acceptable, even though you know it's probably not, (unless your being rude) people usually believe it. So even though I don't know how to act in social scenarios, I know that, and I believe in myself, and people think I'm cool for being weird. If I was insecure about being awkward or weird, then people would shy away from me. People only believe in you socially as much as you believe in yourself.

If you need any more advice, just ask.