I'm 23yo. I have zero experience with girls etc etc. and many of my friends are in the same position, plus most of the people I know are kinda geeky and don't go out much. I suppose I am in a position where I would like to experiment a bit before I get too old. However, going out to bars or clubs alone is not something I've really thought about doing.

I don't feel happy in life and would like to throw out possible ideas for me to change this. This is likely not the most respectable goal, but I wouldn't mind fooling around with some girls while I am still semi-young. So.. noting I don't have any wingmen to help out and my friends don't go out to social places, is it viable to go out alone? I just have zero idea of who I would pick out to talk to, whether I should drink or not, what I can do to make myself look less awkward.

Edit: as prompted in a comment, I've just thought back to a moment a year or so ago where my self esteem took a hit, where I had approached a group of people in a social setting and after some small talk, someone had eventually told me to hang out with my own friends. This is a one-off, but actually turned out to be quite depressing early on (if that hadn't of happened, I may have ended up doing it more frequently back then). Now I am just scared of intruding.