Learn English – How to describe calling someone a “Loser” when you mean it in a “good-natured” way

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How do you describe calling someone a loser in a "nice" way? What word can replace "nice"?

There's a specific word I'm looking for but cannot dig it out of my brain.

"I mean loser in a   _____ way"

It's almost the opposite of "patronising" or "condescending".

Similar words but not quite right:

  • good-natured
  • friendly
  • chummy
  • affectionate
  • sweet
  • nice
  • charming
  • lovable

Context:

Someone calls me this word but I have known this person for a long time and know his humour and what he is like. He says the word often and with a great big smile on his face and arm over my shoulders. I find it funny/laugh when he says it. I am trying to describe this to another person who doesn't quite get it like I feel most people here don't!

Best Answer

Endearing is the best word for the sample sentence. (As the OP commented.)

Sample sentence:

"I mean loser in an endearing way."

Definition:

endearing (adj.) That endears: (a) that wins or inspires affection; (b) manifesting affection, caressing. (OED)

Not sure if that epithet can be sugar-coated though. It strikes me the same as those who would say:

"No offense but...you are a loser."

And, of course, offense is always taken.

Might as well say:

"I'm about to punch you in the nose but you aren't allowed to tear-up, okay?"

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