Making small talk can be easier said than done.

Most of the time though, harmless little questions will do the trick – for most people are dying to talk about themselves.

• Where are you from?
• How was the flight in?
• I went to Hawaii last month, you ever been?
• Do you have kids?

The uncomfortable part can be when none of this works.

I met with a cotton buyer once where I proposed a partnership.

It never panned out, but the initial conversation was one of the most awkward I have ever had.

It was as if he enjoyed the 10 seconds of silence after I asked him a direct question.

In his case, I am not sure it was strategic and considered though – I think he was probably just being a jerk.

But we have all been there to some degree.

On occasion, I find myself struggling through a meaningless discussion too.

Let’s talk about something real – if not – I’d rather be reading a book.

Even if Thiel were just an ordinary investor, dinner with him would make anyone nervous. One quickly finds that he is a man notoriously averse to small talk, or what a friend once deemed “casual bar talk.” Even the most perfunctory comment to Thiel can elicit long, deep pauses of consideration in response—so long you wonder if you’ve said something monumentally stupid. The tiny assumptions that grease the wheels of conversation find no quarter with Thiel. There is no chatting with Peter about the weather or about politics in general. It’s got to be, “I’ve been studying opening moves in chess, and I think king’s pawn might be the best one.” Or, “What do you think of the bubble in higher education?” And then you have to be prepared to talk about it at the expert level for hours on end. You can’t talk about television or music or pop culture because the person you’re sitting across from doesn’t care about these things and he couldn’t pretend to be familiar with them if he wanted to.

-Ryan Holiday, Conspiracy