Owen Waterbury (Kirk Douglas), a bestselling romance novelist, hires aspiring writer Stephanie 'Steve' Gaylord (Laraine Day) as his latest in a long line of attractive, disposable secretaries. Steve's idealistic dreams about socializing with intellectuals and learning more about the creative process soon fade. Her new boss proves more interested in spending time at the race track, carousing with his wisecracking roommate Ronnie (Keenan Wynn) and trying to lure Steve into some after-hours 'dictation.' Understandably enraged, Steve rebuffs his advances and leaves. Prompting Owen to make a determined effort to woo her back, provided he can learn to change his feckless womanizing ways.
Kirk Douglas did not make many comedies. Even fewer good ones. His rugged intensity was best suited to hard-boiled dramas and adventure films. Nonetheless he displays an agreeably light touch throughout this madcap romantic farce, cast largely as the straight man opposite top-billed heroine Laraine Day and an array of zany character players. Among them one-time Thirties crooner Rudy Vallee, Irene Ryan (later 'Granny' in TV sitcom The Beverley Hillbillies), Florence Bates as Owen's overbearing landlady and lovely Gale Robbins as a secretary that stands up for herself. Not that the film gives her character much respect for doing so. Which is among several elements in the script, including Ronnie's lecherous one-liners, Owen hiring a private detective to stalk Steve and the idea that secretaries are just making time till they marry their boss, liable to remind viewers that 1948 was a very long time ago.
Writer-director Charles Martin crams in as much sly innuendo and sexual tension as the Hay's Code allows. Yet beneath the film's frothy good-natured surface lurk uncomfortably acidic undertones. It not only implies Owen routinely seduces then dumps young women but arguably panders to a conservative concept that art is simply a ruse that enables pseudo-intellectuals to get laid. Late in life Kirk Douglas himself took up the pen earning some literary success. Which lends some of his sage self-effacing words here some retroactive authority. There is a nice scene where Owen finally admits to Steve that he gambles and parties largely to delay writing again, frightened as he is of failing to live up to his own hype. Yet it is immediately undone in the next scene when he uses all that truth talk as a pretext towards pouncing on Steve, who happily rebuffs then judo flips him.
Presumably Charles Martin knew precisely what Owen Waterbury was getting at given he was not a particularly prolific writer-director. Beginning with the light comedy No Leave, No Love (1946) (which paired Van Johnson with reoccurring player Keenan Wynn), Martin's small but eclectic filmography includes possibly his best known work the George Sanders starring film noir Death of a Scoundrel (1956) (a fictionalized account of the mysterious death of playboy Serge Rubinstein), racially charged crime drama If He Hollers, Let Him Go! (1968) and racy but still dull con man comedy How to Seduce a Woman (1973). He bowed out with an out of left-field hard-edged action thriller The One Man Jury (1978) starring Jack Palance as a Dirty Harry clone.
Laraine Day's winning personality and undeniable chemistry with a disarmingly boyish Kirk Douglas lend My Dear Secretary what meager charm it has. Though the film starts promisingly it badly loses its way in the second half, devolving into a string of increasingly sour and aimless scenes as Owen blames Steve for a sudden literary slump and continues hiring hot single women. However late in the game the film recovers its balance, making the point of opening Owen's eyes to his foolishness and to Steve's worth and concocts a worthy ending.