A naive young man from Nebraska who moves to New York to start over. He secures a photography job, writes a controversial book on dating based on his experiences, and faces professional and romantic setbacks. Through his journey of loneliness and self-discovery, he learns about genuine connection, ultimately reconciling with his love interest after achieving success.
Direct rival for Sally's affection, creating awkward confrontations at Sally's apartment.
Donald's infatuation with Chandler's girlfriend creates professional and social friction.
Printer and mentor who teaches Donald the business side of publishing and distribution.
Initially adversarial professional dynamic that shifts to a negotiation over paperback rights.
A cabbie who intervenes during a theft and offers Donald initial street-smart advice.
Central romantic pairing that evolves from mutual curiosity to a committed relationship.
Professional relationship where Chandler hires Donald as a photographer.
Longtime friends who reconnect in New York, with Robby acting as Donald's guide to the city.
Explore the full interactive character relationship map of How to Pick Up Girls!