I think I get it now.

Trust.
I think that's all that's wrong with me.
I'm not trusting things to work out right.
There's a reason he agreed. There's a reason he thought about it. He's not doing this to humor me. He's doing this because he thinks it might work. Something might happen.
And all I need to do is trust him. Trust him not to let me down.
...And trusting myself wouldn't hurt, either. :/