Word: 

Words and phrases that rhyme with despairingness:  (6 results)
3 syllables:
daringness, glaringness, sparingness
4 syllables:
unerringness, unsparingness
5 syllables:
overbearingness
Words and phrases that almost rhyme †:  (11 results)
3 syllables:
boorishness, boringness, garishness, meritless, spiritless, spiritous, spirituous
4 syllables:
disparateness, enduringness, unvariedness
5 syllables:
domineeringness
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