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Answer for the clue "Female with chequered history, supposedly maturing by now? ", 8 letters:
fortyish

Word definitions for fortyish in dictionaries

Wiktionary Word definitions in Wiktionary
a. 1 Close to the number forty 2 About forty years old. num. Any number close to forty.

Usage examples of fortyish.

Madeleine Horsekeeper was standing in the doorway greeting them, with a stern-looking fortyish woman standing beside her.

He turned away with a wave and moved towards where he had seen Clementine chatting beside a tall, cadaverous, fortyish bald man with a professorial manner.

A thin, fortyish woman, whose half-tended graying brown hair made her look a decade older, came to the door in answer to Baer's buttonpush.

She was a hefty, nononsense, fortyish individual with a taste for liposuction, face-lifts, and breast augmentation.

A fortyish man named Hudspeth who sported a pencil-thin mustache, he appeared a greasy-looking character who would not have been out of place in an old twentieth-century "smoker": an amateurishly filmed porno flick where the males never bothered to remove their dark socks.

Has any fellow, of the dime a dozen type, it might with some profit some dull evening quietly be hinted--has any usual sort of ornery josser, flatchested fortyish, faintly flatulent and given to ratiocination by syncopation in the elucidation of complications,of his greatest Fung Yang dynasdescendanced,only another the son of, in fact, ever looked sufficiently longly at a quite everydaylooking stamped addressed envelope?

It wasn't much help that both Lance Sheath and MuMu deCharraiveuneuirauville were quite obviously courting-no, probably stalking was the better word -cosmetics heiress Martha Whoopley, a stocky stodgy fortyish styleless frump with the face of a TV dinner and the personality of a humidifier and the ownership of eleven million dollars in her own right.