"one who conceals his opinions, character, etc., under a false appearance, one who pretends that a thing which is is not," 1520s, agent noun from dissemble. "A dissembler is one who tries to conceal what he is; a hypocrite, one who tries to make himself appear to be what he is not, especially to seem better than he is." [Century Dictionary]
c. 1600, "doubtful, questionable, uncertain, unsettled," from French problematique (15c.), from Late Latin problematicus, from Greek problēmatikos "pertaining to a problem," from problēmatos, genitive of problēma (see problem).
Specific sense in logic, differentiating what is possible from what is necessarily true, is from 1610s. The sense of "constituting, containing, or causing a difficulty" is modern, probably from a noun use in sociology (1957). Related: Problematical (1560s); problematically.