Polly Oliver's Problem by Kate Douglas Smith Wiggin
Kate Douglas Wiggin (you might know her from Rebecca of Sunnybrook Farm) gives us a story that feels both of its time and surprisingly fresh. It's a quiet adventure about dignity, resourcefulness, and the lengths we go to for the people we love.
The Story
Polly Oliver's comfortable life is upended when her father loses his money. Faced with the grim prospect of becoming a burden or accepting a marriage she doesn't want, Polly hatches a daring plan. Cutting her hair and adopting the name "Paul," she lands a job as a bellboy at a busy summer hotel. The plot follows her double life: the physical strain of the work, the constant fear of discovery, and the quirky friendships she makes with the hotel staff and guests who have no idea who she really is. It's a story of close calls, small victories, and the heavy weight of a secret.
Why You Should Read It
What grabbed me wasn't just the disguise plot—it was Polly herself. She's practical, brave, and fiercely loyal, but Wiggin lets us see her moments of doubt and exhaustion. The book quietly questions the limited options for "respectable" women in the late 1800s. Polly doesn't put on trousers for fun; she does it out of necessity, because it's the only way she can earn a living wage and keep her family afloat. Her journey is less about fooling everyone and more about discovering her own capability. The supporting cast, from the gruff hotel manager to the various guests, adds warmth and a real sense of place.
Final Verdict
Perfect for anyone who enjoys classic coming-of-age tales with a twist of social commentary. If you liked Jo March's spirit in Little Women or the cleverness of Anne of Green Gables, you'll find a kindred spirit in Polly Oliver. It's a sweet, swift, and ultimately satisfying read that proves some struggles—for independence, family, and self-respect—are truly timeless.