Beautiful Losers is set in Sag Harbor. This small town, located on the east end of Long Island, New York, is part of The Hamptons, an area popular as a summer vacation spot for wealthy New Yorkers. In an earlier book in this trilogy, Rita's comments about her hometown suggested that she was discontented or displeased; in this book she seems quite happy with her "very quiet and friendly town," with its small shops, old hotel, windmill, and harbor. She refers to Sag Harbor as "shabby" but adds "I've always lived here, and so I like it." This mind-set mirrors Rita's own growing acceptance of herself as well.

Much of the story revolves around the home in which Rita and Arnold live. Located on a cliff near the Shelter Island Ferry, the one-room house features a sagging roof, peeling paint, and no bathtub at all; during the cold...