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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!

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    Playful? Joking? Kidding? (And calling someone a name is never nice.) – Tot Zam Aug 8 '17 at 18:33
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    This is neither a synonym for "nice" nor the opposite of "condescending," but I could imagine filling in the blank with tongue-in-cheek. – RaceYouAnytime Aug 8 '17 at 19:00
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    You are assuming the word is being used nastily but the word can definitely be used in a funny/joking manner as a way of affection/endearment. 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! Absolutely appreciate all your word suggestions nonetheless. – Jack Nicholson Aug 8 '17 at 19:23
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    See also "joshing", which is like a joking form of teasing dictionary.com/browse/joshing – Max Williams Aug 8 '17 at 20:10
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    @JackNicholson I see a few comments saying they don't get it, but I'll back you up; a lot of my friends josh each other, and I completely get using a usually negative term (loser, dumbass, etc.) affectionately. It's something that only really works in person, because you need body language, and often physical contact, to get across the full point. You loser (see?). – monoRed Aug 9 '17 at 13:23
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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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  • It can depend on how you word it and the manner at which you say it. Endearing seems to be the best match. Thanks for your help, even though I totally found the word first, loser ;) – Jack Nicholson Aug 8 '17 at 19:38
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    @Jack, yes you did...updated my answer to ref. your comment. – thomj1332 Aug 8 '17 at 19:41
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    :) ...I know. Thanks for checking, though.. I should have noted it anyways. Peace. – thomj1332 Aug 8 '17 at 19:45
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    As a native speaker, endearing does not convey what OP is asking for. Playful banter better suits what he is describing. en.wikipedia.org/wiki/Conversation#Banter – JeffC Aug 9 '17 at 14:13
  • Endearing would mean that you think the person is a loser, but you find that appealing about them. It does not mean you don't honestly think the person is a loser. I think that would be exactly condescending, for which the OP hoped to find an antonym. – Darren Ringer Aug 9 '17 at 14:13
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When I call you a "loser", it's only a bit of banter.

banter ˈbantə/.
noun.
1. the playful and friendly exchange of teasing remarks. "there was much good-natured banter".
— https://en.oxforddictionaries.com/definition/banter

And a second (Irish) one is:

When I call you a "loser", it's only a bit of slagging.

1.1Irish mass noun
Good-natured teasing.
‘there was a bit of slagging but it is all good craic’.
- https://en.oxforddictionaries.com/definition/slagging

Slagging of course has another definition - "An insulting and critical attack.", so depends on the audience if this one works.

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One word for good-natured or light-hearted teasing is ribbing:

Cambridge Dictionary

informal the act of laughing at someone in a friendly way as a joke

YourDictionary.com

the act or an instance of teasing or ridiculing playfully

The word originates from "rib-tickling" or "poking someone in the ribs":

Dictionary.com

"tease, fool," 1930, apparently from rib (n.); perhaps as a figurative suggestion of poking someone in the ribs. Related: Ribbed ; ribbing.

YourDictionary.com

ribing; meaning 'teasing', from the common practice of tickling the ribs to cause laughter.

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Positive!

I mean loser in a positive way!

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    That is about as opposite of "condescending" as you can get. ;) It is, however, not what the OP is looking for (despite the wording used in their request), as "loser" can never truly be a positive label. Saying this would really only make the situation more awkward, as it amounts to a sort of sarcastic acknowledgement that you insulted them without an accompanying apology. – jpmc26 Aug 9 '17 at 1:20
  • I don't know, there is a show called the Biggest Loser where the biggest loser is viewed positively. – Devil07 Aug 9 '17 at 2:23
  • There isn’t really a positive way of interpreting “loser”. It can be endearing or tongue-in-cheek … but not positive. – Konrad Rudolph Aug 9 '17 at 12:10
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    @Devil07 The show The Biggest Loser is about weight loss where "losing" (being a loser) is the goal. – JeffC Aug 9 '17 at 14:10
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    Although it's not easy for me to imagine the "loser" label being applied in a positive context, I wouldn't go so far as to assert it could "never" be the case. The Biggest Loser television show makes an interesting counterexample. @JeffC - I'm pretty sure Devil07 knows why "biggest loser" is viewed positively on that show. – J.R. Aug 9 '17 at 15:26
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The way I see it, there are two primary ways to indicate that a potentially insulting statement is meant to be taken without offense:

  1. Make it clear that the statement is meant to be humorous or joking.

  2. Make it clear that the statement is friendly.

Humor

characterized by insincerity, irony, or whimsical exaggeration

I mean loser in a tongue-in-cheek way

meant to be humorous or funny : not serious. a facetious remark

I mean loser in a facetious way

free from care, anxiety, or seriousness

I mean loser in a lighthearted way

intended for one's own or others' amusement rather than seriously.

I mean loser in a playful way

Friendliness

being pleasant and at ease in talking to others

I mean loser in an affable way

good-natured, cheerful

I mean loser in a good-humored way

marked by kindness and courtesy

I mean loser in a gracious way

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Benign? harmless?

But are you sure the word is loser? How can someone be a loser in a nice way?

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    Thanks for the answer @Stick figure. It's not that one is a loser in a nice way but that you don't mean it in a horrid way. You mean it in more of an endearing way. – Jack Nicholson Aug 8 '17 at 19:19
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    Perhaps affable? jovial? amicable? Good luck finding the word you're looking for. – Stick figure Aug 8 '17 at 19:25
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How about being economical with the gunpowder as in being careful planning where to spend ones energy and time to not burn out too fast on things one probably can't affect anyway.

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