The word pre-possessing - rather more than the modern prepossessing - has been used a lot in Clarissa, at least so far. The book last mentioned at reference 2. A word applied to a lady who has already taken a fancy to a gentleman, so she is already in his possession, is pre-possessed, at least figuratively, and is no longer fair game for any other gentleman. That is to say, rogues and bounders apart. Furthermore, it was no longer really proper for either her friends or her relations to offer her up to some other gentleman that they might have thought appropriate - this sort of marriage brokering being quite common, at least in polite society, at the time of writing, that is to say the middle of the eighteenth century.
Not the modern usage of the word at all, at least if the cartoons above are anything to go by, so I consulted OED. More precisely, Volume VII, Part II, PH to PY, where the word and its relations something more than a column, with the verb getting something more than half of that. It seems that the word came in in the middle of the seventeenth century, in the sense of physical possession of places and things. As in 'I came up to the castle with my forces, meaning to take possession, but finding it prepossessed, I drew off again'. The word then moved onto persons and their attachments. It then moved on to a prior feeling about something, either a good feeling or a bad feeling. Otherwise prejudiced for or against. And from there, the bad fell away, leaving us with the positive adjective, prepossessing.
Oddly, for a book described as one of the great English novels, it is not cited at all, even though the citations which are there include several from the eighteenth century. We get no closer than Jane Austen.
PS: Windows behaved a little oddly when I was lifting the cartoons included above. Perhaps they were trying to stop me so doing.
Reference 3: Clarissa; or, The History of a Young Lady: Comprehending the Most Important Concerns of Private Life. And Particularly Shewing, the Distresses that May Attend the Misconduct Both of Parents and Children, In Relation to Marriage – Samuel Richardson – 1748.
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