I don’t know... my WH has never been a romantic man or good at organising stuff to surprise me and I always accepted it. Luckily he didn’t surprise his ow either (our MC asked him once if he always treats his women badly). Don’t get me wrong he’d buy me stuff but on the basis of “what do you want for your birthday?”.
Now I expect more of him. If he’s changing he needs to do it in this area also, accept and understand that I like to see he thought of me. Since DDay 1 he’s done a lot of stuff in this direction but still no surprises. In fact we had a huge argument at Christmas that he didn’t do anything meaningful for me (a card, a photo album) he got me a perfume.
But what he does is still showing willingness to change. Since DDay 1 he bought me everything I laid eyes on. Which is a bit ridiculous because I told him he cannot “buy me”. But I understand his thought process: all his life he’s been careful with money. If you don’t need it you don’t buy it type of attitude. You don’t buy stuff just because you want it. So now I have a wardrobe full of new clothes (it was needed as I lost lots of weight), a new car, handbags and all sorts because I only dared looking at something and he bought it. He enjoys getting me to try stuff on and then buy it.
So I do appreciate his desire to change and show me he is a new person who puts me first though obviously spending money will not change what happened.
What I would say is, why do you have to tell him everything, don’t we think it should be normal for our loved ones to think of us on a milestone birthday? And if you think you would be too disappointed in case he doesn’t raise to your expectations, would it be easier if you just ask him: “what are you planning for my birthday? Do I need to go outfit shopping for a party evening, or outfit shopping for a romantic holiday?” but maybe once you explain you expect him to go out of his comfort zone on organising something spectacular, don’t tell him what? Surely he should know what you would like and you deserve? Maybe I am still a dreamer...