[PropMike]

This is tldr/emo/and a bit self absorbed, but whatever.

I can relate pretty closely to OP. I am incredibly socially anxious in almost all settings. I have zero small talk and I am not sure why. In group settings I almost always sit on the fringes and chime in from time to time. Even around some close friends I can have difficulty connecting one on one.

What really bothers me is that I don't understand why or how it has become like this. Throughout high school I had a very large group of friends and was well liked. Stupid as it sounds to mention, I was voted as having best sense of humour in my high school year. People generally were interested in what I thought about things and I was happy expressing my opinions. Since then, though (I'm 5 years out of high school) things have gone to [censored]. I just find myself incapable of talking about much, and most of the people I have formed connections with are, if not simple themselves necessarily, interested in simple things. I'm not at all witty. I rarely have deep philosophical/political/whatever discussions with anyone (I studied philosophy and politics at uni, fwiw). I'm not depressed, and I still get by okay, but it's very frustrating.

Anyway, I offer that as context. In my view, or at least in my case, it's not something I think that can be remedied through external things alone. I mean, I've often thought the answer was to go out and get more experiences --> become more interesting, but it's never worked. To the extent that I understand my problem I really feel as though I have disconnected somehow from myself. It's hard to explain. But in conversation, and more generally as well, I feel as though I don't really engage or bring my own perspective to what's in front of me the way I used to. I don't ask the same questions, or spot the interesting consequences of someone's opinion, or work out how to connect with someone's style. Instead, in most conversational settings I just feel kinda confronted. If someone's jokey, I'm anxious about getting their jokes and responding in a jokey way as well. If someone offers an opinion on something, I frantically attempt to comprehend where they're coming from and offer an interesting counter-point or whatever. Instead of rolling with the punches I scramble to react/respond. So basically, social interaction for me is usually somewhat panicked. I get by okay most of the time, but it is very rarely a casual or comfortable experience.

The only times I ever don't feel like this is a couple of hours after I get high (the first couple of hours I'm a wreck). That's when I make flippant observations, rant about the greatness of a band/movie/book, discuss philosophical/political issues that interest me, or quiz someone else about the things that interest them. Anyway, most people have smoked pot and experienced similar things, but my point is that this is when I feel myself in many ways. Pot is a useful catalyst for reenergising my enthusiasm for the things that interest me. In everyday life though, for reasons I'm not sure of, that enthusiasm is missing.

So all this is a roundabout way of saying that for those suggesting OP ask more open ended questions/follow local sports teams/take a trip to europe etc., if his issues with social anxiety are anything like mine it's likely that these tips treat the symptoms and not the cause. To the extent that I understand my problem, it most certainly stems from something internal. It's always good to have things to talk about, but when I come to a conversation with prearranged conversation topics, or a 'strategy' or whatever I invariably feel like I'm running around in circles. It's when I feel confident and engaged in a conversation that it's always more fruitful, and working out how to flip the switch in my mind to make social situations more comfortable is the key.

Anyway, just my perspective on things.