[adj. bit-er-sweet, bit-er-sweet; n. bit-er-sweet]
both bitter and sweet to the taste: bittersweet chocolate.
both pleasant and painful or regretful: a bittersweet memory.
Also called woody nightshade. a climbing or trailing plant, Solanum dulcamara, of the nightshade family, having small, violet, star-shaped flowers with a protruding yellow center and scarlet berries.
Also called climbing bittersweet. any climbing plant of the genus Celastrus, bearing orange capsules opening to expose red-coated seeds, especially C. scandens.
pleasure mingled with pain or regret: the bittersweet of parting.

1350–1400; Middle English; see bitter, sweet

bittersweetly, adverb
bittersweetness, noun Unabridged
Based on the Random House Dictionary, © Random House, Inc. 2014.
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World English Dictionary
bittersweet (ˈbɪtəˌswiːt)
1.  any of several North American woody climbing plants of the genus Celastrus, esp C. scandens, having orange capsules that open to expose scarlet-coated seeds: family Celastraceae
2.  another name for woody nightshade
3.  tasting of or being a mixture of bitterness and sweetness
4.  pleasant but tinged with sadness

Collins English Dictionary - Complete & Unabridged 10th Edition
2009 © William Collins Sons & Co. Ltd. 1979, 1986 © HarperCollins
Publishers 1998, 2000, 2003, 2005, 2006, 2007, 2009
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Word Origin & History

late 14c., as a noun; used especially in M.E. of a type of apple, from bitter + sweet. As an adjective, attested from 1610s.
Online Etymology Dictionary, © 2010 Douglas Harper
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Example sentences
As a professor, attending graduation ceremonies and parties is always a
  bittersweet experience for me.
He made it his theme tune, adapting its originally bittersweet words to the
  needs of the time.
Uncover the bittersweet story of this ancient treat.
Fill peanut-butter cookies with bittersweet chocolate, caramel sauce, and
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