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pinksoil said:
but I figure if I pitch it to him that way, how can he not respond positively?

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It seems like, at least a little bit, you are trying to manipulate him into giving you a particular response that you really want. My T sometimes talks about the need to give each other space to exist and respond authentically (both in therapy and outside with others). I think with your strategy, you aren't really doing this. How about just saying, "I really liked the CD you gave me and I thought you might like to hear some music that is important to me and that I think you'd like," and then hand him the CD. Then he has the space to respond genuinely and accept your gift (or not). Sure, there's more risk of rejection using this strategy, but his acceptance will be more meaningful if he has more choice in it. I really think since he gives you gifts, he will accept your CD!