Bitter
Both words in one sentence
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Even after a barrage of very awful tragedies she's still a Cool Big Sis, to the bitter end.
Source: Cool Big Sis -
Eventually, he was revealed to be a crotchety, bitter fellow teacher in a wig who was attempting to subvert Cool Teacher.
Source: Cool Teacher - In a way, she's his opposite: while Mike only falters on the rare occasions when he loses his cool, April is at her scheming best when she's most bitter and desperate.
Cite this Source
Cool and Bitter. (2016). Retrieved 2026, August 07, from https://thesaurus.plus/related/bitter/cool
Bitter & Cool. N.p., 2016. Web. 07 Aug. 2026. <https://thesaurus.plus/related/bitter/cool>.
Cool or Bitter. 2016. Accessed August 07, 2026. https://thesaurus.plus/related/bitter/cool.
Google Ngram Viewer shows how "bitter" and "cool" have occurred on timeline