D.P.
It's all about unexpressed or unrealistic expectations. See some great responses to my recent post about this.
If he doesn't listen to you (stops listening) and does nothing to show you how he feels (romantically) then what makes you insanely happy?
You're right--no O. is a mind reader, and to 'wish' he J. "knew" what to do to make you happy is an unrealistic expectation! He will fail and fail and disappoint you and disappoint you without him ever knowing!
As for what issues should be discussed and which should be left alone--I think if these two particular topics have caused you to ask anonymous women for advice, they probably need to be discussed, right?