I can think of two times my husband really blew it. When we were first together, well, he is/was an athlete, and I am not. He always had really cool workout clothes, and I thought (silly me) that maybe if I had some cool clothes maybe I'd be more inclined to be active. So I asked him for a sweat suit.
He got me a pair of basic, gray, baggy sweats. Couldn't have been more unromantic or uninspiring.
Some years later, I told him I wanted a bracelet, but I really wanted a bangle, because I DID NOT want a chain bracelet. Yep, I got a chain -- because bangles were too expensive. I cried that time, but I wore that darn chain until it broke (finally).
On the bright side, he remembered a ring I had liked in a jewelry shop and got one for me (custom made) some 10 years later on a big birthday. He gets top marks for that. And he bought me a beautiful inlaid necklace (looks like a quilt almost) while he was on a golf trip in Hawaii. I didn't feel he owed me anything, but I guess he did.
All in all, he's a keeper!