What’s so hard about small talk?

When it comes to “intellectual conversations” I tend to be able to participate pretty well, at least if I have an opinion on the matter. Or conversations with a specific subject, like politics, economy, morality, science, technology, computer or whatever. No problem. But as soon as it comes to small talk or talking with each just out of fun or to kill time I suck as hell most of the time. I mean when I’m with my two friends I don’t think about it at all and we don’t even care about what anyone says but it’s still fun for all three of us. But when I’m with my family, or people I know who I rarely see, people I meet for the first time, or also people on SP I have no fucking clue what to do or to say. I do post sometimes but it’s mostly advice or my personal opinion on a subject. Don’t know when I last made a post just for fun, just to participate in “SP life”. My therapist even said on our first meeting she can’t believe me when I tell her I’m shy and suck at small talk; but that’s due to the fact that we talked about specific subjects (i.e. my depression) where I know what to say, so no small talk at all. Most of the time when I try to be funny or do small talk to get to know people they usually ignore me after some time because apparently I either only said stupid non-funny things or I didn’t say anything at all (the awkward silence…).

The weird thing is that when I am with my two friends we DO have fun most of the time and I won’t even stop talking sometimes because it’s so much fun. But we’re “crazy nerds” who laugh about stuff most people wouldn’t even understand. If I’d tell some gaming joke to a cashier at the supermarket they would only look at me like I was some freak and move on to the next one. When I last helped out in our church band there was this bassist around my age and I didn’t say much at all like usual, but after some time we made jokes and had fun saying stupid things and being sarcastic even though he wasn’t into gaming at all – or at least he didn’t say so. He knows I’m kinda weird but we still had honest fun. So I guess I AM actually able to do small talk of some kind, but only if I’m confident enough with the person I am talking to and if this person also understand my crazy humor. That’s unfortunately not the case with 99% of all people I meet.