Most Helpful Girl
This is an easy one. If you feel anomalous derive your confidence from that feeling. Maybe you can't always relate or find common points of interest with a Kardashian fangirl, but, no offence to those girls, it's not the most terrible fate. Having different interests and your actual individual opinions and views on things is never a bad thing, it's actually quite attractive when I first meet a guy. I have the same problem, I know way too much about Robert Plant and too little about Robert Pattinson to be considered a normal girl. But I don't let my individuality become a problem, sure less people are interested in me once I start singing El Condor Pasa as opposed to the latest Katy Perry song but heck, that may have less to do with Simon and Garfunkel and more to do with my singing.
But I digress, keep being different and embrace the anomalous. Strike up conversation about what you saw on the history channel, eventually some amazing woman is going to surprise you and pick up the torch of conversation without batting an eye. When that happens the thousand dull women you frustrated yourself over won't matter. Just keep trying, being "behind the times"/"out of the loop" just means you have a well established sense of identity and intelligent women appreciate that. So take some confidence from that.