During my lunch breaks, I occasionally play one of the junior members in a game of chess. I'm one of the better players at my school.

I played against an alledged prodigy in the junior years and I was playing the black pieces. It went 1. e4 c5 2. Nf3 d6 3. e5?!

This is my dilemma. I know my main Sicilian lines and I'm sure he did as well. But this move really stumped me and after 10 moves, I was in a terrible position. I did not know how to react to 3. e5?!

Does anyone else have the problem of knowing their book moves and theory, and when you play against a "lower" rated opponent and they make a move out of book, you do not know how to respond to it?

Anyway, back to the game. The middlegame was horrible for me. We entered the endgame. I had K+R+R vs his K+Q+R+P. It was my luck that my endgame knowledge, tactics and preparations were more developed than his and I converted the losing engame into a draw. I say he is an alledged prodigy because he is the best player in the junior years, easily able to defeat another junior member and also playing chess at a club. But he does manage to have good games against me and my chess crew when he challenges us. My record against him currently is 12 wins, 2 losses and 6 draws.

My biggest dilemma is still trying to respond to "out of book" moves in the opening. I know GM's have an easy time punishing moves like 3. e5?! in the Sicilian. For me this is quite complex. Anyone have any suggestions?

3 e5 isnt very good after 3....dxe5  4 Nxe5  Nd7 , black should try to trade the N/e5 or make it retreat.

Does anyone else have the problem of knowing their book moves and theory, and when you play against a "lower" rated opponent and they make a move out of book, you do not know how to respond to it?

Sure.

A pet peeve of mine was when a book would say, "Of course not ___" with no explanation of why ___ was a bad move. Sometimes, I could figure it out, othertimes I'd end up yelling (in vain) at the book asking "WHY NOT???"

I may be wrong about this, but I recall hearing that a favorite ploy Fischer used was to dig up old lines that had been refuted so long ago that the refutations were no longer in the book, and play them because his opponents didn't know "why not."

It is generally advisable to concentrate on learning how to play chess first, and only to start looking at theory when you're pretty strong on your own. Take a lesson from the prodigy -- obviously he doesn't care about any theory, but he did still reach a winning game.

It's not necessarily easy to punish this move; white moves the same pawn twice, but then black hasn't developed anything yet either. Why would it be easy to punish?

Perhaps 3...d5, aiming to play 4...Bg4 and 5...e6 is ok, to get to a sort of French with the problem of the white squared bishop solved. It does cost a tempo (a bit like the 1.e4 c6 2.d4 d5 3.e5 c5 Caro-Kann line), but it's nice that there is already a knight on f3 to pin.

Also 3...dxe5 4.Nxe5 should be considered (it feels like that ought to be the point of 2...d6), but right now I don't see a plan for black that would benefit from this.

Don't obsess over "book moves" too much. All games leave theory at some point, and most of them do so pretty quickly.