These days, I've been constantly playing against the Reckless Dave personality of NagaSkaki.
The personality configuration is as follows:
I usually play G/30 games, allowing the personality to ponder (think on my time). The hash size I maintain in 32 MB.
Initially when I played White against Dave, I used to open with 1. Nf3, and then play either 2. g3 3. Bf2, or 2. d4 depending on Dave's response. One of the reasons I chose to use that opening was because I had read an interesting article about it, and clearly understood the underlying concepts: the Fianchetto -- letting one (or both) Bishops control the longest diagonal(s) -- along with the possibilty of swaying into a Queen side attack after castling short. Moreover, the opening seemed as playable by Black as by White, which was quite an attractive reason to try it out.
As I played and analyzed my several games, I realized that some of the positions resembled the ones I had read about a long time ago, before I had completely given up trying to memorize opening moves. It was then that I understood what transposition meant. Some openings could transpose into others with a different move order, and understanding the concepts underlying one could easily help understand the others. When I was consistently able to beat Dave with the above opening (playing White or Black), I decided to try my hand at what, once upon a time, used to scare the living daylights out of me: the Queen's Gambit.
The Queen's Gambit was one opening that used to make me very nervous when I played Black, and I had never understood how to play it as White. Reading the theory had not helped beyond giving me a headache or a complex. And yet, here I was, after all these years, returning to play the Queen's Gambit as White with a newfound confidence and nothing but the general opening principles. Surprisingly, it no more seemed so baffling. I was not nervous and, though I lost my first game against Dave, I was smiling because I knew exactly what mistakes I had committed that had cost me the game. And a few games later, I was actually winning. Then I switched sides and got Dave to play the Queen's Gambit against me (it can be done by manipulating the opening book used by the application). I was playing my worst fear, but for some reason, I was no more afraid!
I now have two ways to go forward: I can either start playing the next personality (one level higher) of NagaSkaki with whatever understanding I have earned thus far, or try experimenting with another challenging opening at the same level and gain some more experience. I plan to walk the second path, and to try playing with and against the King's Gambit. Hope I am doing right. Suggestions from more experienced players are welcome.