Some things are made to hack and some things just aren't. You are wanting to hack something that just wasn't ever meant to be hacked.
The solution to your problem is so simple it's actually rather elegant: Just care about the other person. If you genuinely care, you'll have no problem finding things to talk about. You'll be asking questions, not because you're following a flowchart or playing a game, but because you really want to know. Fortunately, it's also the only way that works anyway; if you don't care, you'll be clocked and look like a fool.
OTOH, if you don't care about the other person, move on and save both of you the trouble.
Getting to know a person isn't a technical skill that you master and practice at will. (Granted, parts of the process, like choosing interesting topics and getting a feel for what the other person wants to talk about is sort of a skill gained by practice).
Really getting to know a person requires you to actually care what the other person thinks. Almost all else will follow.
Someone here mentioned that they dislike smalltalk so much that they forget the other person's name right after the smalltalk ends. That's just one example of many of what happens if you contrive to talk to someone without actually caring about them.
The solution to your problem is so simple it's actually rather elegant: Just care about the other person. If you genuinely care, you'll have no problem finding things to talk about. You'll be asking questions, not because you're following a flowchart or playing a game, but because you really want to know. Fortunately, it's also the only way that works anyway; if you don't care, you'll be clocked and look like a fool.
OTOH, if you don't care about the other person, move on and save both of you the trouble.