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It sounds like you're having trouble communicating, can you ask him to help you with this? I suspect he could.
It seems what might be holding you back is the belief that you don't have anything interesting to say/your life isn't interesting. I can see how this would hold you back in sharing things, when you're afraid he won't be interested. I don't know if it will help, but maybe keep in mind that you're not there to entertain him, and that's not why they're in this business either. I think most of us want our therapist to like us, though, and I do get that.
I think you must be 'interesting' because you're a human being, however corny this sounds. I think an apparently insignificant event or interaction that just happened last week could end up having a great deal of meaning. Some people have mentioned the metaphor of an onion; I suspect you have many layers, and can use therapy to peel them off one by one, little by little. This takes time and we all have a lot of layers.
If you find yourself talking about certain things because you think he might find it/you interesting -this is understandable, but the important thing is for you to feel better, live a fuller life (maybe), etc. I suspect if you get to the heart of what's causing your pain (some from the past, maybe, but lots of other things as well, I suspect), then you can get to the core of you, and that's always worth exploring, always interesting. Therapy is good for this, most people never get that deep into themselves; it's worth spending the time to get there, and worth it for therapists as well, I would think.
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