prepossessing

From pre- +‎ possess. Attested in 1610s with the meaning of "getting possession of (ground or land) beforehand". The meaning "to possess (a person) beforehand with a feeling, notion, etc." developed in 1630s, acquiring by the 40s of the same century the meaning of "to cause (someone) to have a favorable opinion of something, preoccupy the mind or heart of".

prepossessing (comparative more prepossessing, superlative most prepossessing)

1. Tending to invite favor; attracting confidence, favor, esteem, or love; attractive

   a prepossessing manner

   • 1815, Jane Austen, Emma, volume II, chapter 15:

     "I am a great advocate for timidity—and I am sure one does not often meet with it.—But in those who are at all inferior, it is extremely prepossessing."

   • 1836, “Boz” [pseudonym; Charles Dickens], “The curate. The old lady. The half-pay captain”, in Sketches by “Boz,” Illustrative of Every-day Life, and Every-day People. , volume (please specify |volume=I or II), London: John Macrone, , →OCLC:

     Our curate is a young gentleman of such prepossessing appearance, and fascinating manners, that within one month after his first appearance in the parish, half the young-lady inhabitants were melancholy with religion, and the other half, desponding with love.

   • 1851 June – 1852 April, Harriet Beecher Stowe, “chapter 2”, in Uncle Tom’s Cabin; or, Life among the Lowly, volume (please specify |volume=I or II), Boston, Mass.: John P[unchard] Jewett & Company; Cleveland, Oh.: Jewett, Proctor & Worthington, published 20 March 1852, →OCLC:

     These natural graces in the quadroon are often united with beauty of the most dazzling kind, and in almost every case with a personal appearance prepossessing and agreeable.

   • 1931, H. P. Lovecraft, chapter 3, in The Whisperer in Darkness:

     He was a frank, prepossessing fellow, but I saw that he could add nothing to his original account.

   • 1944 January and February, E. R. McCarter, “The Cairn Valley Light Railway”, in Railway Magazine, page 48:

     The stations are generally very poor, even for a branch line; some are mere wooden shacks, and Moniaive itself is one of the least prepossessing terminal stations I have ever seen.

2. (archaic) Causing prejudice.

• “prepossessing”, in Webster’s Revised Unabridged Dictionary, Springfield, Mass.: G. & C. Merriam, 1913, →OCLC.
• prepossessing, in Etymonline