Play Girl 1941

Grace Herbert, Grace Herbert, is a woman in her 40s who has built her living by seducing wealthy men and suing them for breach of promise. With her loyal maid, Josie, Margaret Hamilton, she heads to Miami as funds dwindle, hoping to land another rich mark. When that plan falters, Grace and Josie stumble upon Ellen Daley, Mildred Coles, a young woman seeking a secretary job. Grace decides to take Ellen under her wing as a protégé, determined to teach her the delicate art of money-making by luring older, affluent men and coaxing sizable settlements to avoid lawsuits. The trio’s journey then carries them north to Chicago, and along the way they cross paths with Tom Dice, James Ellison, a rough-edged cowboy who fixes their flat tire and becomes a quiet catalyst in the evolving plan. Grace initially treats Tom as a mere obstacle or amuse-bell, but Ellen feels a spark of attraction that Grace partially dismisses while she maps out Ellen’s future.

In Chicago, Grace introduces Ellen to Bill Vincent, Nigel Bruce, a vain man who favors younger women and who can fund Ellen’s supposed dreams. Grace coaches Ellen on exactly how to lead a man on enough to extract luxurious gifts and, if necessary, secure a hefty settlement to settle a potential suit. Ellen’s reluctance begins to dissolve as she discovers the thrill of the game and the possibility of wealth, though she still clings to a growing, genuine feeling for Tom. The two women press on to New York City, where they meet Van Payson, G. P. Huntley, another wealthy gentleman who enjoys the spectacle of a much younger companion. During a date, Ellen and Tom share a cab after a brief moment of separation, and Tom expresses interest in seeing her again. Grace, still wary and calculating, scolds Ellen for chasing what she calls a dream, insisting the man is “just a cowboy.” Yet after some careful digging, Grace learns Tom’s true status: he is a multi-millionaire, and the landscape of Ellen’s prospects shifts dramatically. Grace’s mindset flips from caution to a stronger push: Ellen should marry Tom for his wealth.

Ellen loves Tom but balks at marrying under Grace’s manipulative framework and the shadow of her past schemes. When Tom proposes, Ellen asks for time to think, and that night she leaves a note for Grace and vanishes. Grace pivots quickly, deciding to renew her old game with Tom and to salvage a future for herself through his wealth. Meanwhile, Tom’s mother, Mrs. Dice, Katharine Alexander, visits Grace, and instead of delivering threats, she openly acknowledges Grace’s history but offers a blessing if Grace commits to loving and caring for Tom. This uneasy moment acts as a mirror, softening Grace and revealing a flicker of genuine sentiment. Tom, visiting Grace later, learns that his mother supports the idea of the union if Grace truly loves him, and he rushes to Miami in hopes of salvaging a wedding with Ellen.

The plot thickens as Grace’s scheming shifts toward a more calculated, final act. Tom’s uncle—an equally wealthy cattleman—is in town, and Mrs. Dice hints that he could be drawn into a life where grace and femininity temper his bachelor existence. Grace sees a perfect opportunity to bring him into the web, instructing Josie to summon him to Grace’s suite so that she can finalize the arrangement. As the confrontation of old grifts and new loyalties looms, the tension culminates in a quiet, dramatic moment of realization and choice. Grace, facing the possibility of losing Tom to Ellen and the consequences of her own past, faces her own resolve and the pathway to a different future. For the last time, she steadies her breath and prepares for the final play. > “For the last time.”