Choices and Setting Up To Fail

Lately I've been wondering about my role, and how one can be set up to fail. Now this intro does sound like I am wondering about how my Sir would set me up to fail, and to an extent, I am thinking about that. But the situation at hand is how I set him up to fail, and if that's even within the scope of my role as his submissive.

Recently, Sir and I went to the Renaissance Faire. I was very excited and we did end up having a good time. A few weeks prior to our going, we were at a party and a friend of mine had just come from the Faire. Sir commented on her attire, saying that it was a very attractive look, and that he'd love to see me wearing something like that. (This made me happy for two reasons; I could absolutely accomplish this, and he wasn't comparing me to this woman, or saying that she was attractive over me, etc).

Now, he didn't realize this at the time, but this particular woman and I have quite a history. Long story short, I have some jealousy issues, I suppose and because of this, I really wanted to knock his socks off at the Ren Faire.

The morning of Faire, I laid some clothes options out on the bed, and I asked Sir to choose for me. I had some corsets, a skirt, some scarves, etc. I also had a tie dye dress that I've worn from him before, which for some reason, I threw into the pile of choices. Out of all the options, this is what he chose. The simplest, most un-sexy, least Ren Faire-like garment of the pile.

Really? I thought. Out of ALL the things laid out, this is what was chosen? Well, I hated this choice, and I didn't really want to wear it, but its what was chosen so I put it on. He must have seen the disappointment on my face, because he asked me what was the matter. He asked me if he had made the wrong choice. I repeated my thoughts. Out everything, this is what you want? He said yes, and so I would wear it. With his prodding, I explained to him how I really wanted to impress him, so this choice makes me feel frumpy and not as good as the other girl he commented on (who was supposed to be at the Faire). He said of course that it was ridiculous, because I am beautiful, and amazing, and not a bitchy like she, and he loves me and not her naturally. I know these things in my head, but I still felt uncomfortable. He said that I could change, but once the choice is made, you really can't. This is what he chose, so this is what I will wear. I asked him to choose, and he did. Going back on the choice now would render it invalid; why even ask? And furthermore, why would I give him a choice that I didn't want to live with? By giving him a choice that would be unacceptable to me, I am setting him up to fail in this task. And this makes me wonder if its even my place to ask him to choose.

It's an odd topic. Giving up choice seems like a great way to display a power shift. Something more that I can give him over me. And yet, when I select the choices, I do have some control over the situation. Giving only choices that I like is a bit manipulative... I get what I want in either case. And yet... now I'm sitting in this dress, feeling awful, and I have to live with it. What does one do in this situation? Now Sir feels bad, because he knows its not what I wanted. He remembered how I said I wanted to really blow him away. Now I don't have that choice, and no matter what I wear, it won't matter. I won't change, because I want to please him, but in doing that, I'm making myself miserable at least until I can get over it. Even if I did change, I'd feel bad because it's not what he wanted. Plus, who do I think I am anyway? Asking Sir to choose and then being upset when he makes the "wrong" choice? Yet, I still feel the same way.

From something that was supposed to be fun and innocuous, came this giant issue for our relationship. What the hell would happen if this choice wasn't over an outfit, but over something really important? It also makes me wonder how Doms feel, and empathize. There is a lot of pressure, I suppose, to set things up right. In one instance, I set my Sir up to fail, he "failed" at a choice I gave him, and no one won. On the other hand, doesn't it serve me right? Or maybe I can think of this as a learning experience.

To rectify matters, we did have fun at the Ren Faire at least, and this weekend is a similar faire in which I believe he's allowing me to finally knock his socks off. I really want to impress him, so hopefully it will set these odd feelings right.

I still don't know what to do about choices however. Is it wrong of me to ask him to choose? Maybe asking for him to choose is okay, as long as I'm not quantifying it? No options, no multiple choice... just fill in the blank.