A little history…I’m 28, divorced with two young kids, they live at home. He’s relatively attractive but not my usual type or taste. When there’s a rare exception to that rule, we call it love.
You have to try and explain that your relationship is solid and you're not going to call things off if he has a difference of opinion or speaks his mind or stands up to you (as long as it is done respectfully of course).
Maybe toss him some homework where he has to tell you when he doesn't like something you like to show that the whole thing isn't going to crumble around his ears.
Now, if he doesn't like a band I listen to, he'll keep his mouth shut, no matter what he thinks of it, and would tell his friend off, if he listen to that very same band. I just want him to treat me as he'd like to be treated himself. Let him know you need someone that can be their own person...to feel and express their own opinions rather then feeling a need to agree w/ everything you say whether he truly feels that way or not. Problem with this situation is that you always have to walk like you're on eggs and have to watch what you say in case you offend him since he's always careful not to do the same.
Just flat out tell him what you need out of the relationship and if he still cannot give that too ...you need to accept he's not right for you. Going on a mission to be be a nice guy backfires in the end. I think the best solution is for him to be himself around you.
If it would be to shout and scream and tell him you're listening anyway then it's no wonder he keeps his mouth shut.