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He is a bit on the flabby side.

  1. Is it clear that this is about weight?

  2. Is flabby commonly used this way?

  3. Would "flabby" be seen as a comedic way to describe that someone is overweight?

  4. If the sentence was: He is a bit on the heavy side. Would that sound like the person was more overweight than if flabby was used?

  5. Does "flabby" also tell that the person is weak? If not, is there another similar word that also means that?

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    Have you looked up flabby? It has the specific meaning of 'having soft folds of surplus flesh', implying that the person is obese and/or not in good physical condition. Commented Oct 29, 2020 at 14:35

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Your sentence isn't very idiomatic.

Flabby is about loose skin and extra flesh. It's most commonly used to describe body parts, not people as a whole. It can have a connotation of being overweight, but you can be skinny and still have flabby body parts, because it also has to do with a lack of muscle tone.

If you want to indicate that someone is overweight, "heavy" or "fat" or "overweight" would be more appropriate words.

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