In 1932, an orphan named Roy Sheffield started Ashland Addison Florist Co. by selling bouquets of flowers at a busy Chicago intersection. Eight decades later, the fourth generation of Sheffields is still delivering flowers to customers. The Sheffields have learned how to manage a business that requires a highly delicate touch, both in handling a perishable product and in brokering what can be a very emotional transaction. A flower order—choosing the right arrangement, writing the card—can offer a brief but revealing glimpse into someone’s personal life, and a florist is privy to these moments.