I feel your pain. I get married next May and I am dreading taking my htb s surname. He already uses my surname with we book a table etc as it's easier. He always has to spell his surname. I will spend the rest of my life repeating and spelling my surname. Not to mention that it gets pronounced wrongly all of the time. Our two children have his surname but they are not old enough for it to have caused them any issues yet.
I will be Susan Scaife. Scaife rhymes with waif. However I want us to be one family and I will be taking his name. I can't say I'm looking forward to it though.
I think if it means that much to you then you do need to talk to him. You don't want to spend your life hating your name. He might initially be upset but would be get used to the idea?