Seems like you are trying to win over some one -- this is not how it works. Explore yourself first. Find out what makes you tick at your core. I was always lacking confidence in myself thinking what woman is going to like an IT guy who reads a bunch of philosophy and hates sports -- totally the opposite of a masculine guy..
By putting on a front of trying to impress your date, will bring the opposite effect that you might think. Hence, she's bored. That which is chased, runs away. There are multiple levels to communication, body language, tone of voice, word selection (i.e. flirting), etc, all of which has an instant impact (on first and lasting impressions) of the person who is on the receiving end of that communication (even non verbal, or you haven't even spoken a word to them yet).
Have you worked on your appearance? Taken care of yourself? Become solid in what you KNOW makes you tick. If it's sports, it's sports, if it's philosophy, it's philosophy. It's not what your interests are that will impress some one, it's your lack of neediness and being grounded in yourself. A wit will help you get sex, but ultimately, confidence trumps all (strong silent types get sex as well).