Learn English – Never fail to disappoint

meaningmeaning-in-contextphrase-meaning

When you say "he doesn't fail to disappoint", to me it has a negative meaning as in he always disappoints. But I've heard some people using it as a compliment and in a positive way. So, am I wrong about the meaning or it's the other way around?

For example, Christina said on Voice:

My glam team doesn't fail to disappoint and they took the Monday blues
and turned it into a stunning look any girl would love.

Best Answer

"Never fails to disappoint" in the OP's quote seems to be a good example of what the linguists on Language Log call a misnegation, whereby the utterance means the opposite of what was intended. Here is a sample of the misnegations they analyse:

The Republican Party is now at record low levels of unpopularity.

Boehner and Reid are in an undeclared war and neither is refusing to budge an inch.

There is no limit to what he might not ask.

There are many more of these at: http://languagelog.ldc.upenn.edu/nll/index.php?s=misnegation