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I am looking for a word that captures when something/someone looks funny or silly, but in a positive way.

For example when someone is putting their heart into singing but they aren't very good or their expression looks funny, but overall you can appreciate the positivity of how they must be feeling and watching them makes you feel good as well.

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Sample sentence: She looked so _______ while she was singing.

Another example, when you see/overhear a couple or friends doing/talking about things that makes no sense to you as the outsider looking in, but it makes them laugh/happy, so even though it might actually be ridiculous/funny, it's positive for them and for you watching/hearing.

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Sample sentence: They looked so _______ whenever they were doing something together.

Endearing and adorable have come to mind but this doesn't really capture the funny/silly part. Any suggestions on a more appropriate word or words?

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    Try adding an adverb: “delightfully silly” ... – Jim Mar 4 at 6:49
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    In general, something like "comical" or "goofy" is less negative than "silly", but if someone doesn't want to be seen as silly, then any reference to their silliness is pejorative (as with the example of someone trying to sing a serious song). Using "endearing", "charming", or "delightful", could communicate non-seriousness depending on the context: if someone looks charming or delightful doing a serious thing, then they implicitly don't look serious but still have an appealing quality. There are also words like "quirky" and "kooky" which are adjacent in meaning. – Stuart F Mar 4 at 12:26
  • The first illustration brings to mind the expression 'as daft as a brush'. – Edwin Ashworth Mar 4 at 15:21
  • @Jim I think your comment is the closest to what I'm asking, please convert to an answer and I'll accept it – FrontEnd Mar 5 at 0:03
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There is an American slang in use among teenagers: Adorkable.

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Quirky may be useful in some contexts, but not all. Eccentric may also be used in some cases. In my mind this one tends to be used to describe older men. Some other potentially useful words could be whimsical (fantasy-oriented usage), zany (typically indicates a certain high level of energy as well), or off-beat if you're looking for something that's lower energy, but also unorthodox.

As far as I'm aware, there is not a uniformly positive-associated and also formal word that also identifies something that is peculiar, particularly because (as I'm sure you know) pointing out idiosyncrasies is fraught with making someone feel singled-out.

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Dotty

Adjective. If you say that someone is dotty, you mean that they are slightly mad or likely to do strange things. [mainly British, informal] She was obviously going a bit dotty. Synonyms: crazy, wacky, touched, peculiar.

Not to be confused with dotty in American English

confused, strange, or eccentric, feeble or unsteady in gait or (usually fol. by about or over) very enthusiastic or infatuated

https://www.collinsdictionary.com/dictionary/english/dotty

See also:

late 19th century: perhaps from obsolete dote ‘simpleton, fool’, apparently from Dutch dote ‘folly’.

dotty (adj.) 1812, "full of dots," from dot (n.) + -y (2). Meaning "silly" is from c. 1400, in dotypolle "dotty poll" (i.e. "dotty head"), in which case the first element is from dote (v.).

https://www.etymonline.com/word/dotty

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