different between heartless vs calculating

English

From Middle English hertles, herteles, from Old English heortl?as (“without courage; listless”), equivalent to heart +? -less.

heartless (comparative more heartless, superlative most heartless)

(obsolete) Without courage; fearful, cowardly. [10th–19th c.]
- 1782, Frances Burney, Cecilia, II.iii.7:
  Cecilia then, though almost heartless, resolved upon talking with Mr. Harrel himself […].
(now rare) Listless, unenthusiastic. [from 14th c.]
Without a physical heart. [from 15th c.]
Without feeling, emotion, or concern for others; uncaring. [from 16th c.]
His heartless actions and cold manner left her saddened and feeling alone.

calculating

calculating (comparative more calculating, superlative most calculating)

(not comparable) Having the ability to calculate.
an early calculating device
(especially of a person) Serving one's own interests in an unemotional, analytical manner.

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