Not being able to freely communicate with about half of humanity is definitely a handicap, lol. Nothing that can't be learned though!
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I'm going to echo the suggestion to approach men (and later women) for whatever reason to practice approaching people you don't "have business" with.
Ask a question, comment on something benign (cool shirt?), etc.
And also expand your list of contexts where it's ok to talk to people.
Anywhere that groups of people gather is a good option. Concerts, cafés potentially, parks...as long as you aren't cornering anybody, you should be fine.
Your parents are right. It is absolutely a skill that you should learn. The 'times have changed' crowd just haven't stepped up to the new level of difficulty.
It is not wrong to strike up a conversation with a stranger so long as the setting is appropriate and you pick up on the clues they give on whether the interaction is welcome or not. That is the skill you're learning.
Whether it is technically 'necessary' is debatable, but it is antisocial to flat out avoid doing so by definition.
Think carefully about the pressures of the situation. For example, a smile is usually good, unless they are on a job where they are made to smile by their employer.
Essentially, you are right that its inappropriate to approach somebody without business. But getting to know somebody is legitimate business.
You are also sort of right that it has to be an appropriate context for chatting. But it doesnt have to be explicit. If you cross paths in a public place, 1 critical factor is how quickly you are both moving. If she is hurrying, not good. If she is relaxed, that is good.
Pay attention to the other person. The other person is the unknown factor, so its alright to focus on understanding their perspective. And its never as simple as interested/not interested. Empathy is clutch here.
Attention is an offer. Some people, especially from sick cultures, can be really mean when they reject an offer. Dont take that personally, its really about how disappointed they are with what they themselves receive.
that OP actually cares enough about other people to think this over means he's probably more tolerable than most men in my life
when talking to strangers, really good rule to follow is "don't create a situation for somebody who isn't completely free to leave" as in, they can exit the situation or ignore you without any consequences to their job/ night out/ errands/ enjoyment of shared space
most of the rest of the context usually sorts itself out from there, right?
In my view, cold approaching women you don’t know just because you’re attracted to them is harassment.
I don't agree with this. You can approach women in public and talk to us without it being harassment. If you approach someone and they tell you to leave them alone and you don't or they're obviously uncomfortable and you persist then it's harassment.
For some context: I'm not as old as your parents but I'm older than you (I'm late 30s).
You're not wrong, but you've got a bit of an extreme take on it. I think you and your parents may have different thoughts on what it means to "approach" a woman though. I'm going to use "flirt" to refer to talking to a woman with intent of seeing if they would make a good partner for you and just "talk" to indicate just being friendly with someone.
it is only appropriate for a man to talk to a woman who doesn’t know when the social situation is explicitly designed for meeting strangers
No, it's fine to talk to strangers of any gender in public. Approaching them and flirting with them is not. As long as you can roughly understand when you're making someone uncomfortable and stop it, you're not going to come off as a creep/predator. Stuck in a lineup in a store? Chat with someone beside you, maybe commiserate about how long the line is. If you want to flirt with them, then yes the situations you mentioned are definitely the places to do that.
(sort of an aside: whether "meeting friends of friends" is an appropriate situation to flirt with someone you just met is still situation dependent)
They are adamant that I need to learn to approach women or else I will never find a partner.
Approaching women in random public spaces with the intent of finding a partner is also a pretty bad idea. While it could work, it's definitely creep/predator behaviour so I avoid it. It's very likely to make them uncomfortable, since they're just trying to do their thing not get hit on. This can easily be harassment, though I'm on the fence on whether it's always harassment.
Personally I like to flip the genders on situations like this and ask if I'd want to be the other person in this situation. It's worth keeping in mind that woman have way more statistical reasons to be weary/wary of any interaction with men, though. Regardless, e.g. if some woman was beside me in line and started chatting with me, I'd be fine with it. If some woman came up to me and complimented my shirt, I'd be fine with it. If some woman came up to me, complimented my shirt, and then asked for my number I'd be weirded out (I don't know you, lady). If some woman came up to me and asked me to take out my earbuds to commiserate about how long the line is, I'd be annoyed that I'm missing my music.
Personally I think everyone is wrong here, but none of it in a mean or jerky way, just in perspective .
For your parents, it's definitely a different vibe now, we need to be more socially conscious about walking up to a woman, we should understand that that is inherently a dangerous place for a woman and she is likely on her guard.
That being said, you shouldn't be afraid to speak to women either, that is likely just as bad. Women are just people, they have like and dislikes, and you should talk to them the same way you would anyone.
So, I guess what I'm saying is that the days of pickup lines and sauntering over are gone. But there's absolutely nothing wrong striking up a conversation either, and in fact I encourage it. Notice things, maybe they're wearing a band T-shirt of a band you like, maybe they have a cool sticker on their phone or laptop, show interest. Don't be afraid of them.
Do you ever make small talk with men with whom “you don’t have business?”
I’m assuming yes, you probably do. Speaking with women is the same, just be sure to pick up on cues if they don’t want to speak. In fact, I’d advise you to practice by making small talk with everyone you can, with no agenda, and pay attention to their cues.
just be sure to pick up on cues
Yeah. About that...
The unsatisfying answer: you're both a little bit right.
You're correct that times have changed somewhat. But I think it's overkill to say that "approaching women at all unless you have business with them is disrespectful and borderline harassment".
Of course, context matters a lot. Don't bother women at their jobs, the bank is not a lady zoo. But in a social situation where you would expect to meet other people, it's fine to strike up a conversation with strangers or even ask them out.
However, by your own admission you don't get out much. So I'm assuming you don't get a lot of situations like bars or parties where this would happen. So I would try networking in your community, develop some hobbies, go to functions where you might meet someone in this manner.
As usual, the nuanced answer that doesn't oversimplify the complexities is the best one. Good answer.
I bet women 30-40 years ago would have loved to see this answer too. It's a good thing that the world has changed in this regard.
I have lots of advice but I haven't so much as held someone's hand since 2005. So about twenty years now.
The only advice I have is find women your age and ask your questions to them. See what they say. Then go from there.
I'll just say you probably shouldn't take dating advice from people who haven't done any dating for the last 30-40 years. The world has most certainly changed.
I disagree. While certainly some things differ between generations, human nature is still the same and the world in many regards isn't all that different from 40 years ago.
I don't know OP's parents so I can't speak to them specifically, but I wouldn't automatically discount someone's opinion just because they're a couple decades older.
People are allowed to speak to one another in public. Just be respectful of people’s cues, and that goes for people of all genders.