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In these sentences:

"I'm kinda sad toward those comment"
"I'm kinda 'meh' toward it"

What's the usage of "toward" in this context? Is it even grammatically correct?

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Towards is defined by Dictionary.com as:

with respect to; as regards

It's fairly idiomatic. The example:

"I'm kinda sad towards those comment"

denotes the individuals feelings with respect to "those comment[s]" is "sad".

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In these examples, the speaker is directing their emotion in the direction of the comments or it (whatever it is.) It is definitely colloquial and probably not grammatically correct. However, many people (myself included) do not necessarily pay attention to grammar when speaking informally.

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