Twenty-three years after scoring the winning touchdown for his college football team mild-mannered Harold Diddlebock, who has been stuck in a dull, dead-end book-keeping job for years, is let go by his pompous boss, advertising tycoon J.E. Wagglebury, with nothing but a tiny pension. Harold, who never touches the stuff, takes a stiff drink with his new pal... and another, and another. What happened Wednesday?
Cashier and part-time starving artist Christopher Cross is absolutely smitten with the beautiful Kitty March. Kitty plays along, but she's really only interested in Johnny, a two-bit crook. When Kitty and Johnny find out that art dealers are interested in Chris's work, they con him into letting Kitty take credit for the paintings. Cross allows it because he is in love with Kitty, but his love will only let her get away with so much.
Art editor Madeleine Damian carries on numerous loveless affairs. After a failed relationship with advertiser Felix Courtland, the increasingly depressed Madeleine attempts suicide. When Jack Garet, her secretary and former lover, tries to blackmail her, Madeleine resigns and seeks a reclusive life. Neighbor David Cousins befriends Madeleine, but soon Courtland and Garet discover her whereabouts and disrupt her new life.
Two former nightclub partners are now enlisted in the Army. Sergeant Puccinelli ranks above his former partner, Private First Class Korwin. Puccinelli is desperately trying to get transferred from his dull job to active duty overseas. Meanwhile, all Korwin wants is a pass to see his wife and new baby.