In ambiguous environments, it is best to determine ok-ness on the basis of the people.
Good situations:
You are both doing the same thing—looking at the same genre of books in a bookstore, the same exhibit in a museum or zoo, both walking dogs in a park etc. This makes it easier to talk as you already have one thing in common and you can comment on that to see if they are receptive to conversation.
Something unusual happens—a delay on public transport, something wacky is going on in the quad etc
If you mean quad as in university, you already have a thing in common—you’re at the same university. It is likely to be okay to strike up a conversation.
They’re waiting for something. In a queue or waiting for public transport etc—may be bored
They’re having a cigarette—they probably have time for a quick chat and if you smoke too there’s a kind of unspoken thing with smokers where they will have a chat
Presence of alcohol but not a restaurant
Bad signs:
Person is wearing headphones or reading—they are busy and unlikely to want to talk
They are a woman under 40-ish and you are a dude: potential difficulties, see below.
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So there is a thing with a guy approaching a strange woman—she is likely to inductively infer that you are not just after a friendly chat. The best thing to do is use caution and watch for signals that she doesn’t want to be approached and be ready to back off if your intentions are misinterpreted. A good thing to do here is to make sure that it is immediately obvious that you are talking about something that is not her—comment on your shared situation ahead of saying anything like ‘hello’ or ‘how you doing’. Commenting on the books or the museum exhibit or something like that lets her know that you’re looking at that, not her tits.
In ambiguous environments, it is best to determine ok-ness on the basis of the people.
Good situations: You are both doing the same thing—looking at the same genre of books in a bookstore, the same exhibit in a museum or zoo, both walking dogs in a park etc. This makes it easier to talk as you already have one thing in common and you can comment on that to see if they are receptive to conversation.
Something unusual happens—a delay on public transport, something wacky is going on in the quad etc
If you mean quad as in university, you already have a thing in common—you’re at the same university. It is likely to be okay to strike up a conversation.
They’re waiting for something. In a queue or waiting for public transport etc—may be bored
They’re having a cigarette—they probably have time for a quick chat and if you smoke too there’s a kind of unspoken thing with smokers where they will have a chat
Presence of alcohol but not a restaurant
Bad signs: Person is wearing headphones or reading—they are busy and unlikely to want to talk
They are a woman under 40-ish and you are a dude: potential difficulties, see below.
-
So there is a thing with a guy approaching a strange woman—she is likely to inductively infer that you are not just after a friendly chat. The best thing to do is use caution and watch for signals that she doesn’t want to be approached and be ready to back off if your intentions are misinterpreted. A good thing to do here is to make sure that it is immediately obvious that you are talking about something that is not her—comment on your shared situation ahead of saying anything like ‘hello’ or ‘how you doing’. Commenting on the books or the museum exhibit or something like that lets her know that you’re looking at that, not her tits.