It really depends on the environment.
My general advice - and it is what I actually follow - is that if there is interest from the other side, then you will know it. There are signs, they differ a bit from person to person, but you can at least spot if someone is having a good time in your company.
If in doubt, just don’t do it. Simple as that.
In the same way, they probably know you are interested even without saying it. If you are not getting the correct signs, then you are not getting a positive answer either, so do not bother them with asking.
Stay civil, enjoy the rest of the conversation, have a nice day. 
As environments go, hobbies like Go included, the golden rule imho is to never join a hobby to find a girlfriend/boyfriend … people that do that are not only obviously “thirsty” (pardon the expression), rarely manage it, but they also spoil the mood for the rest of the group.
Join a hobby that you actually like and there are bound to be other people there, possibly from the sex/gender you are interested in dating. Meet them, talk to them, enjoy their company, enjoy your mutual hobby. Then, after you already know each other, you could assess if there are the signs to ask for a date. Things like that either feel natural progression or not. If not, again, just don’t do it.
Stay friendly, enjoy meeting with those people and have fun with your common hobby.
I think that the reasonable approach is to rarely geopardise a good time and a good relation with another person by asking them out. If they are not into you, that is immediately a friendship killer. And even if they are into you and the whole thing doesn’t work out, also “friendship gone”.
Is it worth the risk? Sometime it is, sometimes it is not. That, as you said, depends on the individuals, but I think the general rules are quite simple
Growing up in a village it was perplexing for me to find out later, when I went to larger cities, that a general code of staying civil/cordial and respecting other people’s space, time, hobbies and wishes is apparently still a “faraway goal” instead of a “common sense” kind of thing. But, it is what it is. 
Anyway, as settings go, avoid two things:
a) work (because if you fail (or succeed and then break up), then you will have to work with them for a looooooooooong time)
b) the gym ( women get oogled enough there due to the nature of the activity, least we can do is let them do their hobby without hitting on them too, adding an extra layer of akwardness in an already negatively charged environment )
All the above apply in case someone wants a girlfriend. If you are looking to “get along for one night” I have no experience with that since it is not my kind of thing. Most people nowadays prefer apps for that kind of thing anyway.
@Gia mentioned Hollywood and sadly there is much truth to that, even beyond the “tale not lived”. A lot of people are not only sold on the fantasy, but after being bombarded with it since “day 1” they are invested in it. And since most people cannot measure up to the fantasy (which of us looks like an actor? 
) and the reality cannot measure up to the result either ( “and they lived happily ever after”, but life is a series of more downs than ups, usually ) and then you have resentment towards life in general or people in particular.
Assaults, mental and physical abuse, divorces, families broken and children growing in an unhealthy environment, all because the end result didn’t measure up to “the dream”.
Isn’t it a bit ironic that most people kept accusing the violent films of “affecting young people negatively” when in fact most negative feelings seem to have been generated by the perpetual fantasy sold by much more “innocent looking films”. It is a bit sad to watch, else I’d have found the irony very amusing. 
(long story)
