"Ken, you make a good point...however, informing him of my weekend...gives away all my cards. Isn't he supposed to "wonder" sometimes?"
i dont believe you are at the stage where you should worry about making him "wonder".
the issues you have with your R are much larger than that.
you need to learn to communicate, to be independent, to learn patience, to separate business and relationships -- all of which should be done before you worry about making him wonder.
to me, you're too busy playing these games. you're constantly trying to prevent reactions or fabricate reactions.
i think what you need is honesty. i see that from him, when he tells you he wants to take care of the financials first.
"In a ham and eggs breakfast, the hen is involved, but the pig is committed".