happy cringe

When something is really cringy yet it still manages to make you smile, maybe because it was nice or sweet.

Person 1: I'm going to be the entire planet soon.
Person 2: You're already my world ;)
Person 3: You just made me happy cringe.

cringe-happy

not feeling any embarrassment even in an apparently embarrassing situation; able to put up with a cringe-worthy situation easily.

At the party, the girl in a frock danced heavily and suddenly felt that she was not wearing her underwear but she did not feel any embarrassment. She was a cringe-happy girl, indeed.