Does “disheartening” have sadder connotations than “discouraging”? [closed]

Your intuitions about these words match the common native speakers' usage.

As very close synonyms, on the strength of sadness, 'disheartening' is a little more sad than 'discouraging'. There's a little extra nuance of despair possibly with the connotations of 'heart' connected with emotions. 'Discourage' is in that same direction, but just not as far.

I really can't say that one is better or worse for your situation, that's up to your own inner feelings. But for the community of users of English, 'disheartening' is a little more sad than 'discourage'.

As to frequency of use and formality, 'disheartening' is not as common as 'discouraging' (in print, from a fifth to a third of the frequency of discouraging). I'd consider 'disheartening' somewhat more formal (or instead educated, which is not necessarily the same thing) than 'discouraging' (I can imagine a football coach using 'discouraging' a little more than 'disheartening', but the neither by the players.