It was my understanding that the more a character PPs in the game, the better he/she will get at it.  I've yet to have a successful attempt.  Is it due to how new I am to the game?  Or is it something that my character needs to get better at through repetition?

i may be related to your sign up answers or you are trying to pick pokcet people with high deffence or having many Body Guards.

The more you PP the better you skill gets. So if you fail it still gets better just not as much as a success.

Pickpocketing is something that will get better with each attempt. Although slowly. It also depends on the answers you started with.

When Pickpocketing, try only attempting ranks that are lower than your own and ones that do not have boydguards.

(Another bit of off topic advice. There is a help forum. ;-)

Jono gives some good advice... though I must admit that my first attempt to PP was on a Made Man (and I ranked really low on the totem) and I banked out with $700.  Then, like four attempts later I failed miserably.  So really... it's a crap shoot.  Yes, you get better with time and practice... but that doesn't mean you'll always come out on top.

I always come out on top. Awesome is never in the submissive position.