Say what you mean and mean what you say

I have had issues with being direct with people my whole life. I am trying to correct those issues late in my life. I am not talking about obfuscating the truth like a used car dealer. That is an issue in its own right. I am talking about not being direct with a person to avoid any confrontation, hurt feelings, or misunderstanding.

Let me give you an example. Last week I was at a networking event in which I didn't fit with the group. When the moderator asked if I was coming back, I said probably not because I couldn't provide the quid pro quo leads that group required. That was direct. Then he said come again anyway, and I deferred to my habit of not being straightforward, and I said I might. I had no intention of coming back.

I have found this evasive maneuver on both sides of sales situations. Both when I am the seller and when I am the buyer. I don't want to uncover objections because I am afraid of rejection.  When I am buying, I don't want to state the real reason so the seller can't reach into his or her repertoire of objection handling closes. I feel I am not ready to make a decision, and I know I can be talking into making a hasty one if I continue the dialog.

So, give me some feedback as to what to say when my wife asks, "do these jeans make my butt look big?".