I'm not sure how lady bits work (well, in this context), but us blokes can generally squeeze a nut and let the good tears roll.
Crying, and all it's implications...

I'm not sure how lady bits work (well, in this context), but us blokes can generally squeeze a nut and let the good tears roll.

Should you cry when its a lost position, or hold on until the end?
Excellent question! When you become good enough, you'll be able to see almost all your positions are lost positions, it's basically the end on move three or four. Therefore, practicing crying will do you much better than reading some silly chess book

i don't cry. i get very upset with myself and get depressed that i suck so much.
If you're not crying, trigs, you're not trying
When do you start crying in a chess game? I want to cry in the opening, but I usually can't make it appear anguishing enough until the end game. I know the pros can cry at just about any move they wish. They're pros. But that is the most erratic part of my game. It's truly unpredictable when I'm going to start crying. How can I learn to cry at the appropriate times in a chess game?