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Longman Dictionary of Contemporary English
prepossessing
adjective
EXAMPLES FROM CORPUS
▪ It is not a prepossessing start, as the following example from my past experience as a social worker suggests.
▪ The Intelligence service was even prepared to give young Hans a second look, even though he was not a prepossessing sight.
The Collaborative International Dictionary
Prepossessing

Prepossess \Pre`pos*sess"\, v. t. [imp. & p. p. Prepossessed; p. pr. & vb. n. Prepossessing.]

  1. To preoccupy, as ground or land; to take previous possession of.
    --Dryden.

  2. To preoccupy, as the mind or heart, so as to preclude other things; hence, to bias or prejudice; to give a previous inclination to, for or against anything; esp., to induce a favorable opinion beforehand, or at the outset.

    It created him enemies, and prepossessed the lord general.
    --Evelyn.

Prepossessing

Prepossessing \Pre`pos*sess"ing\, a. Tending to invite favor; attracting confidence, favor, esteem, or love; attractive; as, a prepossessing manner. -- Pre`pos*sess"ing*ly, adv.

Douglas Harper's Etymology Dictionary
prepossessing

1640s, "causing prejudice," present participle adjective from prepossess. Opposite meaning "causing agreeable first impression" first recorded 1805.

Wiktionary
prepossessing

a. Tending to invite favor; attracting confidence, favor, esteem, or love; attractive; as, a prepossessing manner.

WordNet
prepossessing

adj. creating a favorable impression; "strong and vigorous and of prepossessing appearance"

Usage examples of "prepossessing".

He looked at Doc Savage, and seemed to approve of what he saw, although Doc, in the guise of Dink Masket, fell far short of being the prepossessing figure he normally was.

As I passed through the gate, I was met by a man of prepossessing appearance, dressed in the eastern fashion, who offered to shew me all over the palace, saying that I would thus save my money.

They were not a prepossessing sight: both were smeared and spattered with the foul blood of the wers, and their faces were black with ash.

The door had been opened to admit another soldier-looking man of less prepossessing appearance at first sight and a weather-tanned, bright-eyed wholesome woman with a basket, who, from her entrance, had been exceedingly attentive to all Mr. George had said.

His appearance, after visiting Mrs. Smallweed with one of these admonitions, is particularly impressive and not wholly prepossessing, firstly because the exertion generally twists his black skull-cap over one eye and gives him an air of goblin rakishness, secondly because he mutters violent imprecations against Mrs.

If The Reaver's Posset had been in one of Madrikhor's less prepossessing neighborhoods, it was a beauty spot compared to the place Belmak and the Weasel now led him.

Not the most prepossessing figure and certainly not, by any stretch of the imagination, a big man on campus.

Rexford but infinitely less prepossessing, looked over her spectacles from the large novel she was involved in and said with careful clarity -- as if that question, from a fleeced goat-boy at just that moment, were exactly what she'd expected -- "Yes.