[Veen]

I have a friend who is excellent at this. He starts talking about whatever, someone's clothes, how his day is going, the weather, anything vaguely relevant to the situation.

People often look slightly uncomfortable at first, but they seem to quickly get over it and start to chatter away enthusiastically. I find it fascinating because I'm totally incapable of doing the same thing: usually I'll be standing next to him squirming with embarrassment at the potential for an awkward moment.

[yomly]

I've seen people "get away with murder" - corny jokes, terrible cliches. The term "sheer force of character" comes to mind - if you're confident enough in yourself, you can usually lead social situations/protocols against the grain as if you can establish that fundamentally you mean well most people will eventually go with the flow.

YMMV though, the people I know who can do this were able to do this from very young in age and I liken it to having a skill, except that it's hard to teach and not many people explicitly value it as something to "learn" - people would rather assume it's something innate

[asdkhadsj]

I'm with you. Though, while I've often wanted to do it but I don't avoid it purely due to my awkwardness; I also avoid it because I don't want to be "that person" and bother someone just minding their own business.

Not that any of this is wrong. I'm just explaining my fear in these situations. Awkwardness I can fight through, but fear of awkwardness combined with fear of actually bothering someone.. it just combines to make me think it's not worth doing.